Hydrochloric Acid → 6-Benzyloxy-4-methyl-1H-indole-2-carboxylic acid

HRID 915442Notes

Reaction equation

HRID 915442 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([CH3:17])[CH:13]=[C:12]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:11]=2)=[O:7])C.Cl>C(O)C>[CH2:19]([O:18][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[C:8]([C:6]([OH:7])=[O:5])[NH:9]2)=[C:14]([CH3:17])[CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 227200096-benzyloxy-4-methyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 692802316-Benzyloxy-4-methyl-1H-indole-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 2 M solution of potassium hydroxide in ethanol (0.48 ml, 0.97 mmol) was added to a solution of 6-benzyloxy-4-methyl-1H-indole-2-carboxylic acid ethyl ester (100 mg, 0.32 mmol; PCT Int. Appl. (2001), WO 2001044186 A1) in ethanol (1 ml). The mixture was heated at reflux for 1.5 h, acidified with 1 N HCl and extracted two times with ethyl acetate. The combined extracts were washed with brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gave 90 mg (0.32 mmol, 99%) of the title compound as yellow crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. extractionextracted two times with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2aef00c6c8494b31996d376c84bd79ce
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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