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

HRID 28700Notes

Reaction equation

HRID 28700 reaction equation
[CH3:1][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>>[CH3:1][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 27718626-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11162516N-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide

Procedure

N-(6-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide was prepared from 6-methyl-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 8.63 (s, 1H), 7.81-7.75 (m, 2H), 7.54-7.48 (m, 1H), 7.47-7.40 (m, 2H), 7.28 (m, 1H), 7.20 (d, 1H), 6.99 (dd, 1H), 6.40 (d, 1H), 5.36 (m, 1H), 2.75 (m, 2H), 2.44 (s, 3H), 2.31 (m, 1H), 2.02-1.91 (m, 3H); MS m/z 303 (M−1).

Sources & evidence

ORD record
ord-20f24feca19c469da16c7b95bda6372e
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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