3-Bromoaniline → 847987-95-5

HRID 1437510Notes

Reaction equation

HRID 1437510 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].OC=[C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:6]([C:16]3[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[C:11]=3[NH:5]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 115623-BromoanilineHCID 101871Cyclohexanone, 2-(hydroxymethylene)-

Product 1

HCID 57941535847987-95-5

Procedure

7-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one was prepared 3-bromoaniline (7.6 g, 44 mmol) and 2-(hydroxymethylene)cyclohexanone (4.3 g, 34 mmol) in a similar manner as described above and recrystallization from methanol to isolate 7-bromo isomer to give 280 mg (1%). of a light brown solid. 1H-NMR (DMSO-d6): δ 8.94 (s, 1H), 7.60 (d, 1H), 7.52 (d, 1H), 7.27-7.25 (m, 1H), 3.01-2.98 (m, 2H), 2.68-2.65 (m, 2H), 2.31-2.24 (m, 2H); MS m/z 263, 265 (M+1).

Workup

  1. customrecrystallization from methanol
  2. customto isolate 7-bromo isomer
  3. customto give 280 mg (1%)

Sources & evidence

ORD record
ord-8a8d4e339d7c49a385bcf3153d08eced
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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