P-Anisidine → 2,3,4,9-Tetrahydro-6-methoxy-1H-carbazol-1-one

HRID 898310Notes

Reaction equation

HRID 898310 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.OC=[C:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][C:17]2=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 101871Cyclohexanone, 2-(hydroxymethylene)-

Product 1

HCID 28568112,3,4,9-Tetrahydro-6-methoxy-1H-carbazol-1-one

Procedure

6-Methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one was prepared from p-anisidine and 2-(hydroxymethylene)cyclohexanone in a similar manner as described in Example 1 to give a tan solid. 1H-NMR (CDCl3): δ 8.77 (br s, 1H), 7.32 (d, 1H), 7.06 (d, 1H), 7.03 (s, 1H), 3.88 (s, 3H), 2.98 (t, 2H), 2.66 (t, 2H), 2.28 (quint, 2H); MS m/z 216 (M+1).

Workup

  1. customto give a tan solid

Sources & evidence

ORD record
ord-1c86da2912c14335ae04972508f1796b
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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