4-Chloroaniline → HCID 11383280, compound

HRID 898319Notes

Reaction equation

HRID 898319 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]2=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:21][C:20]3[CH:22]=[CH:23][C:17]([Cl:16])=[CH:18][CH:19]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11383280HCID 11383280, compound

Procedure

6-Bromo-N-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (100 mg, 0.38 mmol) and 4-chloroaniline (97 mg, 0.76 mmol) in a similar manner as described in Example 13 to give 29 mg (20%) of an off-white solid. 1H-NMR (DMSO-d6): δ 11.07 (s, 1H), 7.56 (s, 1H), 7.23 (d, 1H), 7.13-7.08 (m, 3H), 6.71 (d, 2H), 6.20 (d, 1H), 4.76-4.72 (m, 1H), 2.68-2.54 (m, 2H), 1.99-1.85 (m, 2H), 1.80-1.74 (m, 2H); MS m/z (M−1) 373, 375.

Sources & evidence

ORD record
ord-2b917f48e33a47648683e272fd4db448
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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