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

HRID 379724Notes

Reaction equation

HRID 379724 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 98397823-Acetylamino-2-benzoyl-6-chloroindoleYield 41.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-bf541cafd8784442ae8514558254ffe3
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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