Benzoyl chloride → N-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide

HRID 28701Notes

Reaction equation

HRID 28701 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[C:16](Cl)(=[O:23])[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:15][C:16](=[O:23])[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 7412Benzoyl chlorideHCID 177434976-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11336311N-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide

Procedure

N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide was prepared from 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine and benzoyl chloride in a similar manner as described above to give a pale yellow solid (81% yield). 1H-NMR (CDCl3): δ 9.02 (s, 1H), 7.79-7.73 (m, 2H), 7.54-7.48 (m, 1H), 7.46-7.39 (m, 3H), 7.21 (d, 1H), 7.10 (dd, 1H), 6.45 (d, 1H), 5.32 (m, 1H), 2.72 (m, 2H), 2.30 (m, 1H), 2.01-1.90 (m, 3H); MS m/z 323 (M−1).

Sources & evidence

ORD record
ord-dea99171c13245baad076bdad69c796d
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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