P-Anisidine → 6-chloro-N-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine

HRID 898314Notes

Reaction equation

HRID 898314 reaction equation
[Cl: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:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:22][C:21]3[CH:23]=[CH:24][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 6129776-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 113708326-chloro-N-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Procedure

6-Chloro-N-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one and 4-methoxyaniline in a similar manner as described in Example 13 to give 32 mg (21% yield) of a brown solid. 1H-NMR (CDCl3): δ 8.13 (s, 1H), 7.50 (d, 1H), 7.23 (dd, 1H), 7.14 (dd, 1H), 6.92-6.84 (m, 2H), 6.79-6.73 (m, 2H), 4.76 (m, 1H), 3.83 (s, 3H), 2.74 (m, 2H), 2.28 (m, 1H), 2.08 (m, 1H), 1.98-1.75 (m, 2H); MS m/z 325 (M−1).

Sources & evidence

ORD record
ord-7b5a125cfa7046aab1372bdec040d28f
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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