Lithium hydroxide, monohydrate → 2-[(4-Bromo-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylic acid

HRID 2235575Notes

Reaction equation

HRID 2235575 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([C:20]([O:22]C)=[O:21])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:4]([O:24][CH3:25])[CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68582017Methyl 2-[(4-bromo-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate

Product 1

HCID 685813862-[(4-Bromo-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylic acidYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 150 mg (0.371 mmol) of methyl 2-[(4-bromo-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate in 5 mL of tetrahydrofuran and 2.5 mL of water was added 156 mg (3.71 mmol) of lithium hydroxide monohydrate and the reaction was stirred at room temperature overnight and concentrated in vacuo. The thus obtained residue was diluted with water and carefully adjusted to pH 4-5 using 1 N aqueous hydrochloric acid. The resulting solids were filtered, washed with water and dried under high vacuum to give 112 mg (77%) of the title compound as white solids.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe thus obtained residue was diluted with water
  3. filtrationThe resulting solids were filtered
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-6f1c0168e83d47f392775de72ada0e22
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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