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

HRID 1057653

반응식

HRID 1057653 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87e41baeaf174017bbbabc1dcc17b406
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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