Hydrochloric Acid → 5-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid

HRID 1674576Notes

Reaction equation

C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:9]([CH3:22])[CH:8]=2)=[O:4].O1CCOCC1.O.[OH-].[Li+].Cl>O>[CH2:15]([O:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[CH3:22])[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13]2)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester (1.3 g) in a mixed solvent of 1,4-dioxane (40 mL) and water (20 mL) was added Lithium hydroxide mono hydrate (1.8 g) at room temperature and this mixture was stirred at 50° C. for 1 hour. After this reaction mixture was cooled to room temperature, 1 mol/L hydrochloric acid was added. This precipitated solid was collected by filtration, and washed with water, dried under reduced pressure to give the title compound (1.0 g).

Workup

temperatureAfter this reaction mixture was cooled to room temperature
filtrationThis precipitated solid was collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-a7596903ca8e4aed94700594e5715f3f
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003647B2

Reaction notes

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