Potassium Hydroxide → 3-Acetylamino-2-benzoyl-6-chloroindole

HRID 379724ノート

反応式

HRID 379724 の反応式
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7](C(OCC)=O)[C:6]=1[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 183680413-Acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

生成物 1

HCID 98397823-Acetylamino-2-benzoyl-6-chloroindole収率 41.1%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

To a solution of 3-acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole (556 mg, 1.4 mmol) in ethanol/water (3:1, 20 ml) was added KOH (85% pellets, 480 mg, 7.2 mmol) and the mixture was heated at reflux temperature for 1 h. The mixture was cooled and concentrated, and the residue partitioned between water (50 ml) and diethyl ether (100 ml). The organic extract was washed with water (100 ml) and then brine (100 ml). After drying (MgSO4) and removal of solvent, the crude product was recrystallized from dichloromethane/hexane to afford 180 mg (41%) of the title compound as a yellow powder. m.p.: 212-213° C. 1H-NMR (CDCl3) δ: 9.90 (1H, br s), 8.29-8.15 (2H, m), 7.84-7.75 (2H, m), 7.70-7.52 (3H, m), 7.32-7.27 (1H, m), 7.12 (1H, dd, J=1.83, 9.16 Hz), 2.26 (3H, s). IR (KBr) ν: 3400, 1680, 1640, 1520, 1320 cm−1

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue partitioned between water (50 ml) and diethyl ether (100 ml)
  6. extractionThe organic extract
  7. washwas washed with water (100 ml)
  8. customAfter drying
  9. custom(MgSO4) and removal of solvent
  10. customthe crude product was recrystallized from dichloromethane/hexane

出典と根拠

ORDレコード
ord-bf541cafd8784442ae8514558254ffe3
出典データセット
uspto-grants-2001_10
特許番号
US06300363B1

反応ノート

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