3-Methoxyaniline → HCID 11268733, compound

HRID 898339Notes

Reaction equation

HRID 898339 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]2=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=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:24][C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 108243-MethoxyanilineHCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11268733HCID 11268733, compound

Procedure

6-Bromo-N-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (100 mg, 0.38 mmol) and m-anisidine (94 mg, 0.76 mmol) in a similar manner as described above to give 37 mg (26%) of a white solid; 1H-NMR (DMSO-d6): δ 11.04 (s, 1H), 7.55 (s, 1H), 7.23 (d, 1H), 7.12 (dd, 1H), 6.97 (t, 1H), 6.32-6.27 (m, 2H), 6.13 (dd, 1H), 5.96 (d, 1H), 4.76-4.72 (m, 1H), 3.65 (s, 3H), 2.68-2.52 (m, 2H), 2.00-1.87 (m, 2H), 1.82-1.74 (m, 2H); MS m/z (M−1) 369, 371.

Sources & evidence

ORD record
ord-7501b8651d784a76adf7e5fb430c120c
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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