P-Anisidine → HCID 11314723, compound

HRID 898318Notes

Reaction equation

HRID 898318 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][C:21]([NH2:24])=[CH:20][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:21]3[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11314723HCID 11314723, compound

Procedure

6-Bromo-N-(4-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 p-anisidine (94 mg, 0.76 mmol) in a similar manner as described in Example 13 to give 41 mg (29%) of a light brown solid. 1H-NMR (DMSO-d6): δ 811.05 (s, 1H), 7.54 (s, 1H), 7.22 (d, 1H), 7.11 (d, 1H), 6.73-6.66 (m, 4H), 5.48 (d, 1H), 4.70-4.65 (m, 1H), 3.63 (s, 3H), 2.66-2.53 (m, 2H), 1.98-1.89 (m, 2H), 1.79-1.71 (m, 2H); MS m/z (M−1) 369, 371.

Sources & evidence

ORD record
ord-1438ed089af8497dae2224597c800153
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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