Lithium hydroxide, monohydrate → 5-Nitroindole-2-carboxylic acid

HRID 221226

Reaction equation

O[Li].O.C([O:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)=[O:8])C>C1COCC1.CO.O>[N+:18]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:7]([OH:8])=[O:6])=[CH:17]2)([O-:20])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

LiOH.H2O (1.06 g, 46.2 mmol, 2.1 eq.) was added to a suspension of 5-nitro-1H-indole-2-carboxylic acid ethyl ester (II) (5.15 g, 22 mmol, 1 eq.) in THF/MeOH/H2O 1:1:2 (180 ml). The final suspension turned to dark yellow and was stirred at 25° C. After 30 min the solubilization was complete and total conversion was achieved after 6 hours. The reaction mixture was cooled to 0° C. and quenched with HCl 2N until the solution reached pH 5. Organic volatiles were removed under reduced pressure and the white precipitate was filtered and dried to give the compound of formula (III). Yield=4.53 g (quantitative).

Workup

waittotal conversion was achieved after 6 hours
temperatureThe reaction mixture was cooled to 0° C.
customquenched with HCl 2N until the solution
customOrganic volatiles were removed under reduced pressure
filtrationthe white precipitate was filtered
customdried

Sources & evidence

ORD record: ord-0fc560e3f5c74fd9bd4f1d068875e49a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207165B2

Linked notes

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