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

HRID 28699Notes

Reaction equation

HRID 28699 reaction equation
Cl.[CH:2]1([NH2:15])[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH:2]1([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 189718752,3,4,9-Tetrahydro-1H-carbazol-1-amine hydrochloride

Product 1

HCID 11173800N-(2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide

Procedure

N-(2,3,4,9-Tetrahydro-1H-carbazol-1-yl)benzamide was prepared from 2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride and benzoyl chloride in a similar manner as described above to give a pale yellow solid (73% yield). 1H-NMR (CDCl3): δ 8.79 (s, 1H), 7.81-7.75 (m, 2H), 7.54-7.48 (m, 2H), 7.47-7.40 (m, 2H), 7.32 (d, 1H), 7.17 (m, 1H), 7.09 (d, 1H), 6.42 (d, 1H), 5.37 (m, 1H), 2.78 (m, 2H), 2.32 (m, 1H), 2.03-1.91 (m, 3H); MS m/z 289 (M−1).

Sources & evidence

ORD record
ord-94bff5ddf8b440ee874d465fb35b92ca
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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