Citric Acid → 4-[4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl]Benzoic acid

HRID 1051169Notes

Reaction equation

[CH3:1][CH:2]([CH3:22])[CH2:3][NH:4][C:5]1[C:13]2[N:12]=[CH:11][N:10]([C:14]3C=CC(C#N)=CC=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[C:25](O)(=O)[CH2:26][C:27]([CH2:32][C:33](O)=O)([C:29]([OH:31])=[O:30])O>C(O)C>[CH3:1][CH:2]([CH3:22])[CH2:3][NH:4][C:5]1[C:13]2[N:12]=[CH:11][N:10]([C:14]3[CH:33]=[CH:32][C:27]([C:29]([OH:31])=[O:30])=[CH:26][CH:25]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzonitrile (220 mg, 0.758 mmol) in ethanol (14 m L) at rt was added sodium hydroxide (7 N aqueous solution, 14 mL) in one portion. After stirring at 90° C. for 24 h, the mixture is cooled to rt and acidified with citric acid (10% aqueous solution). The precipitate was filtered, and the remaining solid was washed and dried to yield 4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzoic acid as a white solid (215 mg, 91.7%).

Workup

temperaturethe mixture is cooled to rt
filtrationThe precipitate was filtered
washthe remaining solid was washed
customdried

Sources & evidence

ORD record: ord-f0333288206741d9aad53cd72e610361
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388140B2

Reaction notes

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