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

HRID 35131

Reaction equation

HRID 35131 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.F[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].FC1C=CC2[N:27]3[CH2:44][CH2:43][C:42]4[C:28]3=[C:29]([CH:39]=[CH:40][CH:41]=4)[C:30](N3CCN(C)CC3)=NC=2C=1>>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([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:13]([N+:19]([O-:21])=[O:20])[CH:14]=1.[NH2:19][C:13]1[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=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

Participants

5

Reactant 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 1362874-Fluoro-3-nitrotolueneHCID 138232889-Flouro-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Product 2

HCID 212976531-(4-Methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinolineHCID 212976772-[3,4-Dihydro-1(2H)-quinolinyl]-5-methylaniline

Procedure

Starting with 1,2,3,4-tetrahydroquinoline and 2-fluoro-5-methylnitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-methylphenyl)-1,2,3,4 -tetrahydroquinolin-1-yl}]-4-methyl-1-piperazine carboxamide, and 10-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino-[1,8-ab][15]benzodiazepine.

Sources & evidence

ORD record
ord-ac0909971d8449eea6e0428c5ff3bae3
Source dataset
uspto-grants-1988_08
Patent number
US04764616

Linked notes

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