Hydrochloric Acid → 7-hydroxy-2-phenyl-1H-benzoimidazole-4-carboxylic acid

HRID 349469Notes

Reaction equation

HRID 349469 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:10][C:9]=2[C:8]([O:20]C)=[CH:7][CH:6]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[OH:20][C:8]1[C:9]2[NH:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][C:13]=2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 22663468Methyl 7-Methoxy-2-phenyl-1H-benzo[d]imidazole-4-carboxylate

Product 1

HCID 583814087-hydroxy-2-phenyl-1H-benzoimidazole-4-carboxylic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7-methoxy-2-phenyl-1H-benzoimidazole-4-carboxylic acid methyl ester (4.5 g, 15.94 mmol) obtained in step 3 was dissolved in 100 ml of toluene, aluminum chloride (9.56 g, 71.73 mmol) was added thereto and refluxed for 8 hours. The resulting solution was cooled to room temperature, the reaction was stopped by adding 3 N HCl thereto and stirred for 30 min. The precipitate formed was filtered, washed with benzene and dried to obtain the title compound (3.5 g, 13.77 mmol) in a yield of 86%.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with benzene
  5. customdried

Sources & evidence

ORD record
ord-eabafe62ed674ac9afaa87a270ce7a78
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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