Potassium Hydroxide → Methyl N-(2-benzoyl-6-chloro-1H-indol-3-yl)carbamate

HRID 651008Notes

Reaction equation

HRID 651008 reaction equation
[C:1]([C:9]1[N:10](C(OCC)=O)[C:11]2[C:16]([C:17]=1[NH:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[C:13]([Cl:23])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[NH:18][C:19](=[O:20])[O:21][CH3:22])=[CH:15][CH:14]=[C:13]([Cl:23])[CH:12]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69998691Ethyl 2-benzoyl-6chloro-3-[(methoxycarbonyl)amino]-1H-indole-1-caboxylate

Product 1

HCID 9927446Methyl N-(2-benzoyl-6-chloro-1H-indol-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 2-benzoyl-6-chloro-3-[(methoxycarbonyl)amino]-1H-indole-1-caboxylate (step 3, 680 mg, 1.7 mmol) in ethanol (20 ml) was added 2N aqueous KOH (10 ml) at room temperature. After stirring for 2 h, the mixture was concentrated and extracted with dichloromethane (50 ml×2). The combined organic layers were dried (MgSO4) and concentrated to give an crystalline residue. Recrystallization from ethyl acetate/hexane afforded 320 mg (57%/o) of the title compound as yellow solids.

Workup

  1. concentrationthe mixture was concentrated
  2. extractionextracted with dichloromethane (50 ml×2)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customto give an crystalline residue
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-fd66e27772294e2ca950270ee2d5372e
Source dataset
uspto-grants-2001_08
Patent number
US06277878B1

Reaction notes

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