2-Methylbenzoyl chloride → N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2-methylbenzamide

HRID 28698Notes

Reaction equation

HRID 28698 reaction equation
[Br: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]1([CH3:25])[C:17]([C:22](Cl)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=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:15][C:22](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH3:25])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11749400N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2-methylbenzamide

Procedure

N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2-methylbenzamide was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine and o-toluoyl chloride in a similar manner as described above to give a gray solid (19% yield). 1H-NMR (DMSO-d6): δ 11.01 (s, 1H), 8.70 (d, 1H), 7.59 (m, 1H), 7.47 (d, 1H), 7.33 (m, 2H), 7.26 (m, 2H), 7.17 (dd, 1H), 5.34 (m, 1H), 2.65 (m, 2H), 2.42 (s, 3H), 2.07 (m, 2H), 1.87 (m, 2H); MS m/z 383 (M−1).

Sources & evidence

ORD record
ord-60b865b84fbc49f9851229edfdc10c8e
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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