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Methanol → 4-(3,4-Dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylic acid

HRID 2238588
Notes
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Reaction equation

HRID 2238588 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][C:12]2[C:20]3[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=3[CH:15]=[C:14]([C:23]([O:25]C)=[O:24])[CH:13]=2)[CH2:3][CH2:2]1.CO.[OH-].[Li+]>O1CCCC1>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][C:12]2[C:20]3[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=3[CH:15]=[C:14]([C:23]([OH:25])=[O:24])[CH:13]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68687791HCID 68687791, compound

Product 1

HCID 686891664-(3,4-Dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 4-(3,4-dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylate (1.0 g, 2.8 mmol, STEP 1) in methanol (20 mol) and tetrahydrofuran (30 mL) was added 4M lithium hydroxide aqueous solution (4 mL, 16 mmol) at room temperature. After stirring for 5 hours at 60° C., the reaction mixture was concentrated in vacuum. The residue was dissolved with water and acidified (pH=3) with 2M hydrochloric acid. The resulting precipitate was filtrated, and dried in vacuum to afford the title compound as a white solid (0.85 g, 89%):

Workup

  1. concentrationthe reaction mixture was concentrated in vacuum
  2. dissolutionThe residue was dissolved with water
  3. filtrationThe resulting precipitate was filtrated
  4. customdried in vacuum

Sources & evidence

ORD record
ord-85bbf96e3c1849efb6d5fdab2702e3dd
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718809B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes