4-(Trifluoromethyl)aniline → 6-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one

HRID 1437508Notes

Reaction equation

HRID 1437508 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.OC=[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=[O:20]>>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][CH:4]=1)[NH:7][C:14]1[C:15](=[O:20])[CH2:16][CH2:17][CH2:18][C:19]2=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 101871Cyclohexanone, 2-(hydroxymethylene)-

Product 1

HCID 7526026-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one

Procedure

6-(Trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one was prepared from 4-(trifluoromethyl)aniline (5.5 g, 34 mmol) and 2-(hydroxymethylene)cyclohexanone (3.9 g, 31 mmol) in a similar manner as described above to give 2.25 g (29%). of a dark brown solid. 1H-NMR (DMSO-d6): δ 12.05 (s, 1H), 8.11 (s, 1H), 7.56 (s, 2H), 3.00 (t, 2H), 2.58 (t, 2H), 2.19-2.13 (m, 2H).

Workup

  1. customto give 2.25 g (29%)

Sources & evidence

ORD record
ord-14c01197cb624dc4ab1c7d914e31aa96
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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