Hydrochloric Acid → 1-[(Acetyloxy)methyl]-1H-indole-3-carboxylic acid

HRID 1393667Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[H-].[Na+].[C:15]([O:18][CH2:19]Br)(=[O:17])[CH3:16].Cl>CN(C)C=O.O>[C:15]([O:18][CH2:19][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1)(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1H-Indole-3-carboxylic acid (400 mg) was dissolved in N,N-dimethylformamide (6 ml) and cooled to 0° C. Sodium hydride (500 mg) was added to the solution in two divided portions, and the mixture was stirred as such for 30 minutes. Bromomethyl acetate (0.32 ml) was added slowly dropwise thereto, and the mixture was stirred for 15 minutes at 0° C., warmed to room temperature and stirred for 45 minutes. The mixture was cooled to 0° C., and water was added to the mixture which was then acidified by 2 N hydrochloric acid and extracted with ethyl acetate. The extract was dried over sodium sulfate anhydrous and concentrated under reduced pressure. The residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 50:1) to give the title compound (354 mg, Y.:61%).

Workup

stirringthe mixture was stirred for 15 minutes at 0° C.
temperaturewarmed to room temperature
stirringstirred for 45 minutes
temperatureThe mixture was cooled to 0° C.
extractionextracted with ethyl acetate
dry with materialThe extract was dried over sodium sulfate anhydrous
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 50:1)

Sources & evidence

ORD record: ord-d184009954a14e19a2dd781002a6dc3c
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345180B2

Reaction notes

Loading…