Hydrochloric Acid → 4-(3-Butyl-4-cyano-2-methylpyrrole-1-yl)benzoic acid

HRID 1516582Notes

Reaction equation

C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]#[N:17])[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[C:12]2[CH3:22])=[CH:7][CH:6]=1)C.O.[OH-].[Li+].Cl>C(O)C.O>[CH2:18]([C:13]1[C:14]([C:16]#[N:17])=[CH:15][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:23])=[O:3])=[CH:10][CH:9]=2)[C:12]=1[CH3:22])[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 4-(3-butyl-4-cyano-2-methylpyrrole-1-yl)benzoic acid ethyl ester (0.030 g) and lithium hydroxide mono hydrate (0.041 g) in ethanol (2 mL) and water (1 mL) was stirred at 50° C. for 2 hours. To this reaction mixture was added 1 mol/L hydrochloric acid (5 mL), and this mixture was stirred at room temperature for 30 minutes. This reaction mixture was extracted with ethyl acetate, and this organic layer was washed with water, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.027 g).

Workup

stirringthis mixture was stirred at room temperature for 30 minutes
extractionThis reaction mixture was extracted with ethyl acetate
washthis organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-483026c7d8694330be97237363e9c6c9
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227500B2

Reaction notes

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