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

HRID 73331Notes

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-d66292a776d04e9fb20def1f64c5f06e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829040B2

Reaction notes

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