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US4579949A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of pyrrolo[3,4-c]pyrroles

Assignee: BASF Corp
•
Filing: 1983-05-11
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Granted: 1986-04-01
•
Expires: 2003-05-11
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Abstract

Abstract A process for the preparation of 1,4-diketopyrrolo-[3,4-c]pyrroles of the formula ##STR1## wherein each of R 1 and R 2 independently of the other is an isocyclic or heterocyclic aromatic radical, which process comprises reacting 1 mole of a disuccinate with 2 moles of a nitrile of the formula R.sub.1 --CN (II) or R.sub.2 --CN (III) or with 1 mole of a nitrile of the formula (II) and 1 mole of the nitrile of the formula (III), in an organic solvent and in the presence of a strong base at elevated temperature, and obtaining the compound of formula I from the reaction product by hydrolysis. The pyrrolo-[3,4-c]pyrroles are suitable for pigmenting organic material of high molecular weight.

Inventors

  • 👤 Alain C. Rochat
  • 👤 Luigi Cassar
  • 👤 Abul Iqbal

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 23:16
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3415; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C09; C09B; C09B57/00; C09B57/004

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 287 words
A process for the preparation of a 1,4-diketopyrrolo[3,4-c]pyrrole of formula I ##STR58## wherein each of R 1 and R 2 independently of the other is phenyl or said phenyl substituted by one or two fluorine, chlorine or bromine atoms or mixtures thereof, by one, two or three methoxy or methyl groups or mixtures thereof with chlorine atoms, by cyano, by dimethylamino, by trifluoromethyl, by alkoxycarbonyl of 2 to 3 carbon atoms, by tert-butyl, by cyanophenyl, by acetyl or by alkylbenzoyloxy of 11-14 carbon atoms; biphenylyl; naphthyl or said naphthyl substituted by methoxy anthryl; phenanthryl; pyridyl or said pyridyl substituted by methyl or by amyloxy; quinolyl; furyl or thienyl, which consists essentially of condensing an unsymmetrical or symmetrical dialkyl or diaryl succinate, or monoalkyl monoaryl succinate or dicyclohexyl succinate with two moles of nitrile per each mole of succinate, wherein the nitrile is of formula II or of formula III R.sub.1 CN (II) or R.sub.2 CN (III) or is an equimolar mixture of nitriles of formulas II and III; in an organic solvent which is an alkanol, a glycol, an ether, a glycol ether, a dipolar aprotic solvent, an aliphatic hydrocarbon, an aromatic hydrocarbon, benzene substituted by alkoxy or by halogen, pyridine, picoline or quinoline, or a mixture thereof; in the presence of 0.1 to 10 moles of a strong base per each mole of succinate, wherein said base is an alkali metal, an alkali metal amide, an alkali metal hydride, an alkali metal alcoholate or an alkaline earth metal alcoholate; at a temperature of 60° to 140° C., and hydrolyzing the condensation reaction product obtained in water, a lower alkanol, a mineral acid or an organic acid or mixture thereof to form the compound of formula I.
Claim 2
Dependent Claim 287 words
A process for the preparation of a 1,4-diketopyrrolo[3,4-c]pyrrole of formula I ##STR58## wherein each of R 1 and R 2 independently of the other is phenyl or said phenyl substituted by one or two fluorine, chlorine or bromine atoms or mixtures thereof, by one, two or three methoxy or methyl groups or mixtures thereof with chlorine atoms, by cyano, by dimethylamino, by trifluoromethyl, by alkoxycarbonyl of 2 to 3 carbon atoms, by tert-butyl, by cyanophenyl, by acetyl or by alkylbenzoyloxy of 11-14 carbon atoms; biphenylyl; naphthyl or said naphthyl substituted by methoxy anthryl; phenanthryl; pyridyl or said pyridyl substituted by methyl or by amyloxy; quinolyl; furyl or thienyl, which consists essentially of condensing an unsymmetrical or symmetrical dialkyl or diaryl succinate, or monoalkyl monoaryl succinate or dicyclohexyl succinate with two moles of nitrile per each mole of succinate, wherein the nitrile is of formula II or of formula III R.sub.1 CN (II) or R.sub.2 CN (III) or is an equimolar mixture of nitriles of formulas II and III; in an organic solvent which is an alkanol, a glycol, an ether, a glycol ether, a dipolar aprotic solvent, an aliphatic hydrocarbon, an aromatic hydrocarbon, benzene substituted by alkoxy or by halogen, pyridine, picoline or quinoline, or a mixture thereof; in the presence of 0.1 to 10 moles of a strong base per each mole of succinate, wherein said base is an alkali metal, an alkali metal amide, an alkali metal hydride, an alkali metal alcoholate or an alkaline earth metal alcoholate; at a temperature of 60° to 140° C., and hydrolyzing the condensation reaction product obtained in water, a lower alkanol, a mineral acid or an organic acid or mixture thereof to form the compound of formula I.
Claim 3
Dependent Claim 19 words
A process according to claim 1, wherein the nitrile is a single nitrile of the formula II or III.
Claim 4
Dependent Claim 24 words
A process according to claim 1, wherein the disuccinate is a symmetrical dialkyl succinate containing 1 to 18 carbon atoms in each alkyl moiety.
Claim 5
Dependent Claim 20 words
A process according to claim 1, wherein the disuccinate is a symmetrical dialkyl succinate, wherein alkyl is sec- or tert-alkyl.
Claim 6
Dependent Claim 15 words
A process according to claim 1, wherein the solvent is a secondary or tertiary alcohol.
Claim 7
Dependent Claim 15 words
A process according to claim 1, wherein an organic acid is used for the hydrolysis.
Claim 8
Dependent Claim 63 words
A process according to claim 1 wherein each of R 1 and R 2 independently of the other is phenyl or said phenyl substituted by one or two chlorine atoms, by one or two methyl groups, by methoxy, by trifluoromethyl, by cyano, by methoxycarbonyl, by tert-butyl, by dimethylamino or by cyanophenyl; naphthyl; biphenylyl; pyridyl or said pyridyl substituted by amyloxy; furyl or thienyl.
Claim 9
Dependent Claim 43 words
A process according to claim 7 wherein each of R 1 and R 2 independently of the other is phenyl, 3-chlorophenyl, 4-chlorophenyl, 3,5-dichlorophenyl, 4-methylphenyl, 4-methoxyphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-cyanophenyl, 4-cyanophenyl, 4-methoxycarbonylphenyl, 4-tert-butylphenyl, 4-dimethylaminophenyl, 4-(p-cyanophenyl)phenyl, 1-naphthyl, 2-naphthyl, 4-biphenylyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 6-amyloxy-3-pyridyl, 2-furyl or 2-thienyl.
Claim 10
Dependent Claim 15 words
A process according to claim 1, wherein the strong base is an alkali metal alcoholate.
Claim 11
Dependent Claim 19 words
A process according to claim 9, wherein the alkali metal alcoholate is derived from a secondary or tertiary alcohol.

References Cited (Backward Citations)

US4415685A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-03-31 1989-09-30 1990-04-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-03-31 1993-09-30 1994-04-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-03-31 1997-09-30 1998-04-01 $7700.00 Window Closed / Lapsed

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