Aniline → 6-chloro-N-phenyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine

HRID 898313Notes

Reaction equation

HRID 898313 reaction equation
[Cl: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.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 6129776-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 113699616-chloro-N-phenyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Procedure

6-Chloro-N-phenyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one and aniline in a similar manner as described in Example 13 to give 200 mg (74% yield) of a yellow solid. 1H-NMR (CDCl3): δ 8.04 (s, 1H), 7.46 (d, 1H), 7.27-7.20 (m, 2H), 7.17 (dd, 1H), 7.10 (dd, 1H), 6.79 (m, 1H), 6.74 (m, 2H), 4.81 (m, 1H), 3.85 (s, 1H), 2.70 (m, 2H), 2.25 (m, 1H), 2.03 (m, 1H), 1.93-1.78 (m, 2H); MS m/z 295 (M−1).

Sources & evidence

ORD record
ord-204c9ea6f4114bd4be1bc855b5d9747a
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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