US4018763A
Expired / Lapsed
US
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Process for the manufacture of basic oxazine dyes
Assignee: Novartis Corp
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Filing: 1975-04-14
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Granted: 1977-04-19
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Expires: 1995-04-14
Abstract
Abstract A process for the preparation of basic oxazine dyes of the formula ##STR1## wherein R represents a low molecular alkoxy or alkyl group which is substituted or unsubstituted, R 1 represents a low molecular alkyl group which is substituted or unsubstituted, R 2 represents a low molecular alkyl group which is substituted or unsubstituted or an aryl radical, and each of R 3 and R 4 independently represents hydrogen or a low molecular alkyl radical which is substituted or unsubstituted, and R 1 may be attached to R 2 and R 3 to R 4 through a heteroatom, and wherein the ring a can carry further non-ionogenic substituents or a fused benzene ring, and X - represents an anion, which process comprises treating a compound of the formula ##STR2## wherein R 1 , R 2 and a have the meanings previously assigned to them, with nitrous acid in a polar, water-miscible solvent and adding to the resultant nitrosation mixture, without isolating the nitroso compound, a diamine of the formula ##STR3## wherein R, R 3 and R 4 have the indicated meanings and each of R 5 and R 6 represents hydrogen or a low molecular alkyl group.
Inventors
- 👤 Peter Moser
- 👤 Alex Nicopoulos
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 08:40
CPC Classifications
C; C09; C09B; C09B19/00
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
238 words
A process for the preparation of a basic oxazine dye of the formula ##STR27## wherein R is lower alkoxy or lower alkyl, R 1 and R 2 are independently lower alkyl which is unsubstituted or substituted by halo, cyano, hydroxy, methoxy, ethoxy, phenoxy or phenyl; or R 1 and R 2 together with the nitrogen to which they are attached represent piperidino or morpholino, R 3 and R 4 are independently hydrogen or lower alkyl which is unsubstituted or substituted by halo, cyano, hydroxy, methoxy, ethoxy, phenoxy or phenyl, the benzene ring a may be further substituted by halo, methoxy, methyl or a fused benzene ring, and X is an anion which comprises reacting a phenolic compound of the formula ##STR28## with nitrous acid at a temperature below 50° C in the presence of a strong inorganic acid and in a polar, water-miscible solvent selected from the group consisting of lower alcohols, cyclic ethers, lower aliphatic carboxylic acids and an aprotic dipolar solvent having a dipole moment greater than 2.5 and a dielectric coefficient greater than 15, to form the corresponding nitroso compound in the reaction mixture, adding to said reaction mixture, without isolation of said nitroso compound, a diamine of the formula ##STR29## wherein R 5 and R 6 are independently hydrogen or lower alkyl, to form said basic oxazine dye at a temperature between 20° to 120° C, and recovering said dye from the reaction mixture.
Claim 2
Dependent Claim
238 words
A process for the preparation of a basic oxazine dye of the formula ##STR27## wherein R is lower alkoxy or lower alkyl, R 1 and R 2 are independently lower alkyl which is unsubstituted or substituted by halo, cyano, hydroxy, methoxy, ethoxy, phenoxy or phenyl; or R 1 and R 2 together with the nitrogen to which they are attached represent piperidino or morpholino, R 3 and R 4 are independently hydrogen or lower alkyl which is unsubstituted or substituted by halo, cyano, hydroxy, methoxy, ethoxy, phenoxy or phenyl, the benzene ring a may be further substituted by halo, methoxy, methyl or a fused benzene ring, and X is an anion which comprises reacting a phenolic compound of the formula ##STR28## with nitrous acid at a temperature below 50° C in the presence of a strong inorganic acid and in a polar, water-miscible solvent selected from the group consisting of lower alcohols, cyclic ethers, lower aliphatic carboxylic acids and an aprotic dipolar solvent having a dipole moment greater than 2.5 and a dielectric coefficient greater than 15, to form the corresponding nitroso compound in the reaction mixture, adding to said reaction mixture, without isolation of said nitroso compound, a diamine of the formula ##STR29## wherein R 5 and R 6 are independently hydrogen or lower alkyl, to form said basic oxazine dye at a temperature between 20° to 120° C, and recovering said dye from the reaction mixture.
Claim 3
Dependent Claim
25 words
A process according to claim 1, wherein said solvent is dimethyl formamide, dimethyl acetamide, N-methylpyrrolidone, hexamethylphosphoric acid triamide, dimethyl sulfoxide, tetramethylene sulfone, acetone or acetonitrile.
Claim 4
Dependent Claim
12 words
A process according to claim 1, wherein said solvent is dimethyl formamide.
Claim 5
Dependent Claim
46 words
A process according to claim 1, wherein said phenolic compound is of the formula ##STR30## wherein R 1 and R 2 are independently lower alkyl which is unsubstituted or substituted by halo, cyano, hydroxy, methoxy, ethoxy, phenoxy or phenyl, and Y is hydrogen, methyl or methoxy.
Claim 6
Dependent Claim
68 words
A process according to claim 1, wherein said phenolic compound is of the formula ##STR31## wherein R 1 and R 2 are independently lower alkyl which is unsubstituted or substituted by halo, cyano, hydroxy, methoxy, ethoxy, phenoxy or phenyl; or R 1 and R 2 together with the nitrogen to which they are attached represent piperidino or morpholino, and wherein the benzene ring a is not further substituted.
Claim 7
Dependent Claim
14 words
A process according to claim 1, wherein said phenolic compound is 3-dimethylaminophenol or 3-diethylaminophenol.
Claim 8
Dependent Claim
20 words
A process according to claim 1, wherein R 3 , R 4 , R 5 and R 6 are hydrogen.
Claim 9
Dependent Claim
13 words
A process according to claim 1, wherein said diamine is 1,3-diamino-4-methylbenzene or 1,3-diamino-4-methoxybenzene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-18 | 1980-10-18 | 1981-04-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-18 | 1984-10-18 | 1985-04-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-18 | 1988-10-18 | 1989-04-19 | $7700.00 | Window Closed / Lapsed |