1,3-Cyclohexanedione → 6-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057653

Reaction equation

HRID 1057653 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]2=1

Participants

4

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 77023(4-Methoxyphenyl)hydrazine

Product 1

HCID 152128016-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-oneYield 65.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-methoxyphenyl hydrazine (0.359 g, 2.06 mmol) in toluene (30 mL) is added 1,3 cyclohexanedione (0.231 g, 2.06 mmol). The mixture is refluxed for 30 minutes. The toluene is removed under reduced pressure and the residue triturated in CH2Cl2: CH3OH (95:5). A white solid is filtered to give 0.2903 g (65%) of the title compound; IR (drift) 3160, 3141, 3114, 3064, 1619, 1588, 1474, 1434, 1277, 1215, 1140, 1015, 844, 802, 791 cm−1. MS (ESI+) for C13H13N1O2 m/z 216 (M+H)+. 1H NMR (DMSO-d6) δ2.08, 2.39, 2., 3.74, 6.74, 7.25, 7.43; Anal Calcd for C13H13NO2: C, 72.54; H, 6.09; N, 6.51. Found: C, 71.48; H, 6.06; N, 6.45.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. customThe toluene is removed under reduced pressure
  3. customthe residue triturated in CH2Cl2: CH3OH (95:5)
  4. filtrationA white solid is filtered

Sources & evidence

ORD record
ord-87e41baeaf174017bbbabc1dcc17b406
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Linked notes

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