6-Methyl-1,2,3,4-tetrahydroquinoline → 6-Methyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

HRID 34373

Reaction equation

HRID 34373 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].F[C:23]1[CH:46]=[CH:45][C:26]2[N:27]3[CH2:44][CH2:43][C:42]4[C:28]3=[C:29]([CH:39]=[CH:40][CH:41]=4)[C:30]([N:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)=[N:31][C:25]=2[CH:24]=1>>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])[CH2:7][CH2:6][CH2:5]2.[NH2:31][C:25]1[CH:24]=[CH:23][CH:46]=[CH:45][C:26]=1[N:27]1[C:28]2[C:29](=[CH:39][C:40]([CH3:1])=[CH:41][CH:42]=2)[CH2:30][CH2:43][CH2:44]1.[CH3:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([CH:11]=1)[C:30]([N:32]1[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]1)=[N:31][C:25]1[CH:26]=[CH:45][CH:46]=[CH:23][C:24]=1[N:8]3[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 666786-Methyl-1,2,3,4-tetrahydroquinolineHCID 738951-Fluoro-2-nitrobenzeneHCID 138232889-Flouro-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Product 3

HCID 212976566-Methyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinolineHCID 212992501-(2-Aminophenyl)-6-methyl-1,2,3,4-tetra-hydroquinolineHCID 212992545-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]-benzodiazepine

Procedure

Starting with 6-methyl-1,2,3,4-tetrahydroquinoline and 2-fluoronitrobenzene and following steps 1a to 1f of Example 2, one may obtain, in sequence, 6-methyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-aminophenyl)-6-methyl-1,2,3,4-tetra-hydroquinoline, N-[2-(6-methyl-1-phenyl)-1,2,3,4-tetrah quinolin-1-yl]-4-methyl-1-piperazine carboxamide, and 5-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]-benzodiazepine.

Sources & evidence

ORD record
ord-d86be5753d494b37924d2fe3e7fba0ee
Source dataset
uspto-grants-1988_08
Patent number
US04761412

Linked notes

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