Lithium Hydroxide → 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid

HRID 2273593Notes

Reaction equation

[OH-].[Li+].[CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)([CH3:5])[CH3:4]>>[CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)([CH3:5])[CH3:4]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 67514178methyl 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoate

Product 1

HCID 675138974-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoic acidYield 56.6%

Procedure

1 N lithium hydroxide solution (1.2 mL, 1.2 mmol) is added to a solution of methyl 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoate (122 mg, 0.395 mmol). The reaction may be stirred at room temperature overnight and concentrated. 1 N hydrochloride solution may be added to the residue and a white precipitate collected by filtration to give 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid (66 mg)

Workup

customThe reaction
concentrationconcentrated
addition1 N hydrochloride solution may be added to the residue
filtrationa white precipitate collected by filtration

Sources & evidence

ORD record: ord-de828ee67a5e4c21991243f47f0e14bd
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09125901B2

Reaction notes

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