p-Toluidine → HCID 11771325, compound

HRID 898317Notes

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

Participants

Reactant 2

HCID 7813p-Toluidine

HCID 6129776-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11771325HCID 11771325, compound

Procedure

6-Chloro-N-(4-methylphenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one and p-toluidine in a similar manner as described in Example 13 to give 59 mg (41% yield) of a yellow solid. 1H-NMR (CDCl3): δ 8.10 (s, 1H), 7.51 (m, 1H), 7.22 (d, 1H), 7.17-7.06 (m, 3H), 6.72 (d, 2H), 4.82 (m, 1H), 3.74 (s, 1H), 2.74 (m, 2H), 2.33 (s, 3H), 2.27 (m, 1H), 2.07 (m, 1H), 1.98-1.76 (m, 2H); MS m/z 309 (M−1).

Sources & evidence

ORD record: ord-db32ffa793e24ae8b9e50461b3c3b6db
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351733B2

Reaction notes

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