Ethanol → N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide

HRID 545506ノート

反応式

HRID 545506 の反応式
C(Cl)(=O)C.C(O)C.Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:17]N)[CH:14]=[CH:15][CH:16]=1.O=[C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:14]([C:21]3[CH2:22][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])[CH2:24][CH2:25][C:20]=3[NH:17]2)=[CH:15][CH:16]=1

参加物

6

反応物 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

生成物 1

HCID 59161215N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide収率 31.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Follow the procedures essentially as described in Preparation 6, above, using acetyl chloride (26 mL, 360 mmol) and absolute ethanol (90 mL) with 3-methoxyphenylhydrazine hydrochloride (5.24 g, 30 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (5.50 g, 30 mmol). When complete, dilute the reaction with ethyl acetate (200 mL) and wash with 0.5N NaOH and sodium bicarbonate solution. Filter the solids in the organic phase, triturate in dichloromethane and filter to give 2.67 g (31%) gray solid. MS (ES): m/z 287 (M+1), 285 (M−1); 1H NMR(DMSO-d6): δ 10.52 (s, 1H), 7.83 (d, 1H, J=7.5 Hz), 7.21 (d, 1H, J=8.4 Hz), 6.78 (s, 1H), 6.60 (d, 1H, J=8.4 Hz), 4.00 (m, 1H), 3.75 (s, 3H), 2.87 (dd, 1H, J=14.8, 5.1 Hz), 2.76 (m, 2H), 2.48-2.36 (m, 2H), 2.48-2.36 (m, 2H), 1.76 (m, 1H), 1.03 (d, 6H, J=6.6 Hz).

後処理

  1. customas described in Preparation 6
  2. additionWhen complete, dilute
  3. washwash with 0.5N NaOH and sodium bicarbonate solution
  4. filtrationFilter the solids in the organic phase
  5. customtriturate in dichloromethane
  6. filtrationfilter

出典と根拠

ORDレコード
ord-8f72a4b9037442e9b4f7ba28d4052d7b
出典データセット
uspto-grants-2011_05
特許番号
US07935722B2

反応ノート

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