Hydrochloric Acid → HCID 23510098, compound

HRID 1883120Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:6]([CH3:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14]C)[CH:8]=2)=[O:4].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClCCl.C(OCC)(=O)C>[OH:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([C:3]([OH:4])=[O:2])[N:6]2[CH3:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a flask under nitrogen was added 576 mg (2.63 mM) of 6-Methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester and 30 ml dichloromethane. The mixture was cooled to −60° C. in dry ice acetone bath and 16 ml 1M boron tribromide in dichloromethane (16 mM) was added. After stirring 45 minutes at −60° C. the mixture was allowed to warm to room temperature and stirred for 5 hours. The mixture was poured into 200 ml saturated sodium bicarbonate solution and stirred for 30 minutes. Hydrochloric acid was added till acidic, ethyl acetate was added and the mixture filtered through a celite plug to remove insoluble solids. The ethyl acetate layer was separated and the aqueous was extracted two more time with ethyl acetate. The combined ethyl acetate layers were dried over magnesium sulfate, filtered and stripped to give 6-Hydroxy-1-methyl-1H-indole-2-carboxylic acid (M/S, ES-, 190.2 M−H).

Workup

temperatureto warm to room temperature
stirringstirred for 5 hours
stirringstirred for 30 minutes
additionwas added
filtrationthe mixture filtered through a celite plug
customto remove insoluble solids
customThe ethyl acetate layer was separated
extractionthe aqueous was extracted two more time with ethyl acetate
dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
filtrationfiltered

Sources & evidence

ORD record: ord-4a3ad7d51d2f4ca4858a15f6f2cac79d
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759428B2

Reaction notes

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