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1,2,3,4-Tetrahydroquinoline → 1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

HRID 34374
Notes
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Reaction equation

HRID 34374 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:11][C:12]1[CH:13]=[CH:14][C:15](F)=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1.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>>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1.[NH2:31][C:25]1[CH:24]=[C:23]([Br:11])[CH:46]=[CH:45][C:26]=1[N:27]1[C:28]2[C:29](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:30][CH2:43][CH2:44]1.[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[N:27]3[CH2:26][CH2:45][CH2:46][C:42]4=[CH:41][CH:40]=[CH:39][C:29](=[C:28]34)[C:30]([N:32]3[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]3)=[N:18][C:16]=2[CH:17]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 27363284-Bromo-1-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 138129271-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinolineHCID 138129315-Bromo-2-[3,4-dihydro-1(2H)-quinolinyl]aniline
HCID 13812943
10-bromo-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine

Procedure

Starting with 1,2,3,4-tetrahydroquinoline and 5-bromo-2-fluoronitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-bromophenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-bromophenyl)-1,2,3,4-tetrahydro-quinolin-1-yl}]-4-methyl-1-piperazine carboxamide, and 10-bromo-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]-benzodiazepine.

Sources & evidence

ORD record
ord-0757bb5dad3945569ca85fc707fb05cd
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04761412

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes