2-Methoxyaniline → HCID 11349243, compound

HRID 898342Notes

Reaction equation

HRID 898342 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[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=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:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][CH3:16])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 70002-MethoxyanilineHCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11349243HCID 11349243, compound

Procedure

6-Bromo-N-(2-methoxyphenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (200 mg, 0.76 mmol) and o-anisidine (187 mg, 1.52 mmol) in a similar manner as described above and recrystallized from acetonitrile to give 30 mg (11%) as yellow crystals; 1H-NMR (DMSO-d6): δ 11.07 (s, 1H), 7.56 (d, 1H), 7.22 (d, 1H), 7.13 (dd, 1H), 6.84-6.73 (m, 3H), 6.60-6.56 (m, 1H), 4.85-4.80 (m, 1H), 4.72 (d, 1H), 3.73 (s, 3H), 2.70-2.53 (m, 2H), 2.00-1.75 (m, 4H); MS m/z (M−1) 369, 371.

Workup

  1. customrecrystallized from acetonitrile
  2. customto give 30 mg (11%) as yellow crystals

Sources & evidence

ORD record
ord-68478d75639e4f72a76845484ae17968
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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