Reaction #1483077

Reaction equation

3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

sodium hydroxide

methanol

water

→

3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid

Yield 98.0%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   workup.ADDITIONThe remaining residue was diluted with ethyl acetate (20 mL)
3. 3
   Washwashed with 1N HCl (20 mL)
4. 4
   DryingThe organic layer was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

A solution of 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (69 mg, 0.17 mmol), sodium hydroxide (21 mg, 0.52 mmol), methanol (3 mL), water (1 mL) and THF (3 mL) was heated to 60° C. for 24 hr. The reaction solution was then cooled to room temperature and concentrated in vacuo. The remaining residue was diluted with ethyl acetate (20 mL) and washed with 1N HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid (64 mg, 98% yield).

Source