US4026898A
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7-Oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo[3,2-g]q
Assignee: United States Department of the Navy
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Filing: 1976-03-04
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Granted: 1977-05-31
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Expires: 1996-03-04
Abstract
Abstract 7-Oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrol3,2-g] quinoline, a new compound, useful as a blue-green laser dye, is prepared from a substituted indole. It has the expanded formula ##STR1##
Inventors
- 👤 Ronald A. Henry
- 👤 Peter R. Hammond
- 👤 Erhard J. Schimitschek
- 👤 John A. Trias
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 01:34
CPC Classifications
H; H01; H01S; H01S3/00; H01S3/14; H01S3/20; H01S3/213; C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C09; C09B; C09B15/00; C09B57/00
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
3 words
7-Oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline.
Claim 2
Dependent Claim
3 words
7-Oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline.
Claim 3
Dependent Claim
3 words
7-Oxo-1,2,3,3-tetramethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline.
Claim 4
Dependent Claim
3 words
7-Oxo-1,2,3,3-tetramethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline.
Claim 5
Independent Claim
96 words
A method for preparing 7-oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline comprising the steps of: a. hydrogenating under pressure 1,3,3-trimethyl-2-methylindoline with a 10% palladium on charcoal catalyst whereupon the catalyst is removed leaving a liquid; b. forming a reaction mixture by adding with cooling and stirring to said liquid nitric acid and sulfuric acid, whereupon the reaction mixture is neutralized to obtain 6-nitro-1,2,3,3-tetramethylindoline; c. reducing said 6-nitro-1,2,3,3-tetramethylindoline to the corresponding 6-amino-1,2,3,3-tetramethylindoline; d. reacting then refluxing said 6-amino-1,2,3-tetramethylindoline with ethyl trifluoroacetoacetate to yield 7-Oxo-1,2,3,3-tetramethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline; and e. refluxing said 7-oxo-1,2,3,3-tetramethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1H-pyrrolo [3,2-g] quinoline with trimethyl phosphate to yield 7-oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1H-pyrrolo [3,2-g] quinoline.
Claim 6
Independent Claim
96 words
A method for preparing 7-oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline comprising the steps of: a. hydrogenating under pressure 1,3,3-trimethyl-2-methylindoline with a 10% palladium on charcoal catalyst whereupon the catalyst is removed leaving a liquid; b. forming a reaction mixture by adding with cooling and stirring to said liquid nitric acid and sulfuric acid, whereupon the reaction mixture is neutralized to obtain 6-nitro-1,2,3,3-tetramethylindoline; c. reducing said 6-nitro-1,2,3,3-tetramethylindoline to the corresponding 6-amino-1,2,3,3-tetramethylindoline; d. reacting then refluxing said 6-amino-1,2,3-tetramethylindoline with ethyl trifluoroacetoacetate to yield 7-Oxo-1,2,3,3-tetramethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1-H-pyrrolo [3,2-g] quinoline; and e. refluxing said 7-oxo-1,2,3,3-tetramethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1H-pyrrolo [3,2-g] quinoline with trimethyl phosphate to yield 7-oxo-1,2,3,3,8-pentamethyl-5-trifluoromethyl-2,3,7,8-tetrahydro-1H-pyrrolo [3,2-g] quinoline.
References Cited (Backward Citations)
US3005824A
Cited
US3649634A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-30 | 1980-11-29 | 1981-05-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-30 | 1984-11-29 | 1985-05-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-30 | 1988-11-29 | 1989-05-31 | $7700.00 | Window Closed / Lapsed |