p-Toluidine → 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

HRID 1437504Notes

Reaction equation

HRID 1437504 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.OC=[C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17]>>[CH3:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:11]1[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][C:16]2=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 101871Cyclohexanone, 2-(hydroxymethylene)-

Product 1

HCID 6079846-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

Procedure

6-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one was prepared from p-toluidine and 2-(hydroxymethylene)cyclohexanone in a similar manner as described above to give a tan solid. 1H-NMR (CDCl3): δ 8.65 (s, 1H), 7.43 (s, 1H), 7.30 (d, 1H), 7.20 (d, 1H), 2.98 (t, 2H), 2.65 (t, 2H), 2.45 (s, 3H), 2.26 (m, 2H); MS m/z 220 (M+1).

Workup

  1. customto give a tan solid

Sources & evidence

ORD record
ord-c0732d6be53d4743805336efc9995407
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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