2-(4-nitro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester → 2-(4-amino-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid

HRID 349503Notes

Reaction equation

HRID 349503 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[NH:10][C:9]=2[C:8]([O:23]C)=[CH:7][CH:6]=1)=[O:4].[H][H]>CCO.[Pd]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[NH:10][C:9]3[C:8]([OH:23])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[N:12]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 586241902-(4-nitro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 691318362-(4-amino-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-nitro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester (0.63 g, 1.92 mmol) obtained in step 2 was dissolved in 15 ml of EtOH, 0.1 g of 10% Pd/C was added thereto and stirred for 24 hours while hydrogen was supplied thereto from a balloon fulfilled with H2 gas. The resulting solution was filtered and dried to obtain the title compound (0.57 g, 1.92 mmol) in a yield of 100%.

Workup

  1. filtrationThe resulting solution was filtered
  2. customdried

Sources & evidence

ORD record
ord-5a5dd8c5dc184962ab6dc5d438d3f494
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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