US4622400A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of certain m-aminophenols and the use thereof for preparation of laser dyes
Assignee: United States Department of Energy
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Filing: 1983-12-29
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Granted: 1986-11-11
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Expires: 2003-12-29
Abstract
Abstract Methods are provided for making certain m-aminophenols using a sulfonation/alkali fusion procedure. The aminophenols are key intermediates in the synthesis of dyes, particularly efficient, stable dyes for laser application. Preparations of some rhodamine and phenoxazone dyes from the m-aminophenols are described.
Inventors
- 👤 Peter R. Hammond
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:25
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/12; C07D491/14; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/36
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
107 words
A method for preparing a compound of the Formula I: ##STR21## wherein R is hydrogen or linear or branched alkyl of 1 to 10 carbon atoms, comprisihg the steps of: (a) treating the compound of the Formula IA ##STR22## with a sulfonating agent selected from the group consisting of fuming sulfuric acid and acid sulfates at a temperature below about 40° C. by gradual addition of said compound of the Formula IA to an excess of said sulfonating agent to form a 7-sulfonated derivative of IA; (b) converting said 7-sulfonated derivative to a sulfonate salt; and (c) fusing the product of step (b) with alkaline metal hydroxide.
Claim 2
Independent Claim
107 words
A method for preparing a compound of the Formula I: ##STR21## wherein R is hydrogen or linear or branched alkyl of 1 to 10 carbon atoms, comprisihg the steps of: (a) treating the compound of the Formula IA ##STR22## with a sulfonating agent selected from the group consisting of fuming sulfuric acid and acid sulfates at a temperature below about 40° C. by gradual addition of said compound of the Formula IA to an excess of said sulfonating agent to form a 7-sulfonated derivative of IA; (b) converting said 7-sulfonated derivative to a sulfonate salt; and (c) fusing the product of step (b) with alkaline metal hydroxide.
Claim 3
Dependent Claim
16 words
A method according to claim 1 wherein R is alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
10 words
A method according to claim 2 wherein R is methyl.
Claim 5
Independent Claim
125 words
A method for preparing a compound of the Formula I ##STR23## wherein R is a linear or branched alkyl of 1 to 10 carbon atoms, comprising the steps of: (a) treating quinoline with an alklating agent to form N-alkylated quinoline; (b) hydrogenating said N-alkylated quinoline to form 1,2,3,4-tetrahydro N-alkyl quinoline; (c) treating said 1,2,3,4-tetrahydro N-alkyl quinoline from step (b) with a sulfonating agent selected from the group consisting of fuming sulfuric acid and acid sulfates at a temperature below about 40° C. by gradual addition of said tetrahydro N-alkyl quinoline to an excess of said sulfonating agent to form a 7-sulfonated derivative thereof; (d) converting said 7-sulfonated derivative to a sulfonate salt; and (e) fusing said 7-sulfonated derivative from step (d) with alkaline metal hydroxide.
Claim 6
Independent Claim
125 words
A method for preparing a compound of the Formula I ##STR23## wherein R is a linear or branched alkyl of 1 to 10 carbon atoms, comprising the steps of: (a) treating quinoline with an alklating agent to form N-alkylated quinoline; (b) hydrogenating said N-alkylated quinoline to form 1,2,3,4-tetrahydro N-alkyl quinoline; (c) treating said 1,2,3,4-tetrahydro N-alkyl quinoline from step (b) with a sulfonating agent selected from the group consisting of fuming sulfuric acid and acid sulfates at a temperature below about 40° C. by gradual addition of said tetrahydro N-alkyl quinoline to an excess of said sulfonating agent to form a 7-sulfonated derivative thereof; (d) converting said 7-sulfonated derivative to a sulfonate salt; and (e) fusing said 7-sulfonated derivative from step (d) with alkaline metal hydroxide.
Claim 7
Dependent Claim
30 words
The method of claim 4 wherein said step (b) is conducted utilizing a hydrogenating agent selected from the group consisting of platinum, Raney nickel, sodium borohydride, and tin and HCl.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-11-10 | 1990-05-12 | 1990-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-11-10 | 1994-05-12 | 1994-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-11-10 | 1998-05-12 | 1998-11-11 | $7700.00 | Window Closed / Lapsed |