3,4-Dichloroaniline → HCID 11338824, compound

HRID 898345Notes

Reaction equation

HRID 898345 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.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Cl:24])[NH2:20]>>[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:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:24])=[C:17]([Cl:16])[CH:18]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11338824HCID 11338824, compound

Procedure

6-Bromo-N-(3,4-dichlorophenyl)-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 3,4-dichloroaniline (245 mg, 1.51 mmol) in a similar manner as described above to give 12 mg (4%) of an off-white solid; 1H-NMR (DMSO-d6): δ 11.08 (s, 1H), 7.57 (d, 1H), 7.26 (d, 1H), 7.23 (d, 1H), 7.13 (dd, 1H), 6.92 (d, 1H), 6.70 (dd, 1H), 6.52 (d, 1H), 4.79-4.77 (m, 1H), 2.68-2.52 (m, 2H), 1.99-1.72 (m, 4H); MS m/z (M−1) 409.

Sources & evidence

ORD record
ord-f10a45fce9214f548236f13664936c4c
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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