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

HRID 28695

Reaction equation

HRID 28695 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](Cl)(=[O:25])[C:17]1[C:18]([O:23][CH3:24])=[CH:19][CH:20]=[CH:21][CH:22]=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:16](=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11749912N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2-methoxybenzamide

Procedure

N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2-methoxybenzamide was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine and o-anisoyl chloride in a similar manner as described above to give a pale orange solid (67% yield). 1H-NMR (CDCl3): δ 9.06 (s, 1H), 8.31 (d, 1H), 8.25 (dd, 1H), 7.60 (d, 1H), 7.46 (m, 1H), 7.20 (dd, 1H), 7.17 (dd, 1H), 7.10 (m, 1H), 6.96 (d, 1H), 5.31 (m, 1H), 3.91 (s, 3H), 2.72 (m, 2H), 2.31 (m, 1H), 1.98 (m, 3H); MS m/z 399 (M−1).

Sources & evidence

ORD record
ord-a4f90bfa6c7d4880b21f4783b84c0ba7
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Linked notes

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