HCID 178418361, compound → HCID 178430523, compound

HRID 1019074Notes

Reaction equation

HRID 1019074 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[C:6]([CH3:12])=[C:5]([N+:13]([O-])=O)[CH:4]=1)#[N:2].[H][H]>CO.[Pd]>[NH2:13][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[C:6]=1[CH3:12]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178430969HCID 178430969, compound

Product 1

HCID 178430523HCID 178430523, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-cyano-4-methyl-5-nitrobenzimidazole (0.91 g, 4.5 mmol) and 10% palladium-on-carbon (100 mg) in methanol (200 mL) is treated with an atmosphere of hydrogen (1 atm, balloon) for 14 hours. The resulting mixture is filtered through Celite and rotary evaporated. The residue is purified by flash chromatography (silica gel, 95:5 ethyl acetate:methanol) to afford 5-amino-7-cyano-4-methylbenzimidazole.

Workup

  1. filtrationThe resulting mixture is filtered through Celite and rotary evaporated
  2. customThe residue is purified by flash chromatography (silica gel, 95:5 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-8fea9ded25904dafb16cf66c47b89271
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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