US4302599A
Expired / Lapsed
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Process for nitrating anilides
Assignee: Merck Sharp & Dohme LLC
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Filing: 1979-09-10
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Granted: 1981-11-24
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Expires: 1999-09-10
Abstract
Abstract This invention describes a novel process whereby meta-substituted anilides are nitrated in the para position in high yields.
Inventors
- 👤 Lydia Peer
- 👤 Joseph Mayer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 10:57
CPC Classifications
C; C07; C07C; C07C231/00; C07C231/12
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
94 words
The process for para nitrating a meta-substituted anilide wherein the meta-substituent is selected from the group consisting of lower alkyl, lower acyl, polyfluoro lower alkyl, nitrogen and halogen; which comprises subjecting said meta-substituted anilide to a mixed acid solution consisting of nitric acid and oleum wherein the reaction temperature is maintained at from about -20° C. to about 50° C., the nitric acid is present at from about 1 to about 4.5 moles per mole of anilide and the oleum is present at from about 1.5 to about 10 milliliters per gram of anilide.
Claim 2
Dependent Claim
94 words
The process for para nitrating a meta-substituted anilide wherein the meta-substituent is selected from the group consisting of lower alkyl, lower acyl, polyfluoro lower alkyl, nitrogen and halogen; which comprises subjecting said meta-substituted anilide to a mixed acid solution consisting of nitric acid and oleum wherein the reaction temperature is maintained at from about -20° C. to about 50° C., the nitric acid is present at from about 1 to about 4.5 moles per mole of anilide and the oleum is present at from about 1.5 to about 10 milliliters per gram of anilide.
Claim 3
Dependent Claim
22 words
The process according to claim 1 including the steps of isolating and hydrolyzing the para-nitro-meta-substituted anilide to yield the corresponding meta-substituted-para-nitro aniline.
Claim 4
Dependent Claim
23 words
The process according to claim 1 wherein the oleum has a sulfur trioxide content by weight of from about 5% to about 40%.
Claim 5
Dependent Claim
43 words
The process of claim 3 wherein the nitric acid is present at from about 1 to about 1.2 moles per mole of anilide and the oleum is present in the ratio of from about 2.5 to about 7 milliliters per gram of anilide.
Claim 6
Dependent Claim
35 words
The process of claim 4 wherein the nitrating step is conducted for from about 1/2 to about 2 hours and the sulfur trioxide constitutes from about 10% to about 25% by weight of the oleum.
Claim 7
Dependent Claim
20 words
The process of claim 2 wherein m-trifluoromethylisobutyranilide is nitrated to produce 3'-triflluoromethyl-4'-nitroisobutyranilide and hydrolyzing said compound to yield 3-trifluoromethyl-4-nitro aniline.
Claim 8
Dependent Claim
14 words
The process of claim 1 wherein m-trifluoromethyl isobutyranilide is nitrated to produce 3'-trifluoromethyl-4'-nitro isobutyranilide.
Claim 9
Dependent Claim
14 words
The process of claim 1 wherein m-chloro isobutyranilide is nitrated to produce 3'-chloro-4'-nitro isobutyranilide.
Claim 10
Dependent Claim
14 words
The process of claim 1 wherein m-bromo isobutyranilide is nitrated to produce 3'-bromo-4'-nitro isobutyranilide.
Claim 11
Dependent Claim
14 words
The process of claim 1 wherein m-fluoro isobutyranilide is nitrated to produce 3'-fluoro-4'-nitro isobutyranilide.
Claim 12
Dependent Claim
14 words
The process of claim 1 wherein m-nitro isobutyranilide is nitrated to produce 3',4'-dinitro isobutyranilide.
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) | 1984-11-23 | 1985-05-25 | 1985-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-23 | 1989-05-25 | 1989-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-23 | 1993-05-25 | 1993-11-24 | $7700.00 | Window Closed / Lapsed |