Water → Methyl indole-6-carboxylate

HRID 2068866Notes

Reaction equation

HRID 2068866 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[C:13](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O.CCCCCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 639844Methyl indole-6-carboxylateYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 1H-indole-6-carboxylic acid (121 g, 752 mmol) in N,N-dimethylformamide (360 ml) was added potassium carbonate (124 g, 900 mmol), and the mixture was stirred at room temperature for 1 hr. Then, iodomethane (56 ml, 900 mmol) was added dropwise at room temperature over 15 min, and the mixture was stirred for 2 hr. Then, to the reaction solution were added water (1.2 L) and hexane (100 ml), and the mixture was stirred at room temperature for 1 hr. The precipitated crystals were collected by filtration, washed successively with water and hexane, and dried under reduced pressure to give the title compound (115 g, yield 87%).

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed successively with water and hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c2b060ec7d6d4b9983f5e188cff866da
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

Loading…