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

HRID 1057653

反応式

HRID 1057653 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-87e41baeaf174017bbbabc1dcc17b406
出典データセット
uspto-grants-2003_02
特許番号
US06514968B1

関連ノート

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