4-Chloro-1-fluoro-2-nitrobenzene → 5-Chloro-2-[3,4-dihydro-1(2H)-quinolinyl]aniline

HRID 34375

Reaction equation

HRID 34375 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.[Cl: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>>[Cl: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]([Cl: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.[Cl: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

Participants

6

Reactant 3

HCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 694601,2,3,4-TetrahydroquinolineHCID 138232889-Flouro-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Product 3

HCID 196245085-Chloro-2-[3,4-dihydro-1(2H)-quinolinyl]anilineHCID 2012910810-chloro-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepineHCID 212976471-(4-Chloro-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

Procedure

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

Sources & evidence

ORD record
ord-37f9a56e4374462ea8f84b378b5fce66
Source dataset
uspto-grants-1988_08
Patent number
US04761412

Linked notes

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