Reaction #502103

Reaction equation

indole-6-carboxylic acid

N,O-dimethylhydroxylamine hydrochloride

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

pyridine

→

compound

Yield 107.3%

N-Methoxy-N-methylindole-6-carboxamide

Yield 107.3%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   ConcentrationThe mixture is concentrated
2. 2
   WashThe organic phase is washed with 50 ml of a 1N solution of sodium hydroxide and 50 ml of a saturated solution of sodium chloride
3. 3
   Dryingdried over magnesium sulphate
4. 4
   Concentrationconcentrated under reduced pressure

Procedure

In a round-bottomed flask, 5.0 g of indole-6-carboxylic acid, 3.3 g of N,O-dimethylhydroxylamine hydrochloride, 11.9 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 10 ml of pyridine are placed in 150 ml of tetrahydrofuran. The mixture is stirred at ambient temperature for 40 h. The mixture is concentrated, and the residue is taken up in 150 ml of ethyl acetate and 50 ml of water. The organic phase is washed with 50 ml of a 1N solution of sodium hydroxide and 50 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. 6.8 g of compound are obtained.

Source