Water → 1-Methylindole-3-carboxylic acid

Temperature

0 °C

1H-Indole-3-carboxylic acid (960 mg) was dissolved in N,N-dimethylformamide (15 ml) and cooled to 0° C. Sodiumhydride (720 mg) was added in two divided portions thereto, and the mixture was warmed to room temperature and stirred for 1 hour. The mixture was cooled again to 0° C., and a solution of methyl iodide (0.67 ml) in N,N-dimethylformamide (5 ml) was added slowly dropwise thereto, and the mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was cooled to 0° C., then ice was added thereto, water (50 ml) was further added thereto, and precipitated crystals were collected by filtration and washed with water and n-hexane. The product was dried under reduced pressure to give the title compound (910 mg, Y.:87%) as yellow crystals.

1. temperaturethe mixture was warmed to room temperature
2. temperatureThe mixture was cooled again to 0° C.
3. temperaturethe mixture was warmed to room temperature
4. stirringstirred for 2 hours
5. temperatureThe reaction mixture was cooled to 0° C.
6. additionice was added
7. customprecipitated crystals
8. filtrationwere collected by filtration
9. washwashed with water and n-hexane
10. customThe product was dried under reduced pressure

ORD record

ord-3eb74125083e4d369a8a6589ec5f036b

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345180B2