Formic Acid → Methyl 1H-benzimidazole-4-carboxylate

HRID 1505756Notes

Reaction equation

HRID 1505756 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:15](O)=O>[Pd]>[NH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[N:1]=[CH:15]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 14970852Methyl 1H-benzimidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 2-amino-3-nitrobenzoate (1.0 g) in formic acid (>87%) was added 5% palladium on carbon (100 mg) and the suspension was heated with stirring at 100° C. for 23 hours. After the reaction mixture was cooled to room temperature, the catalyst was filtered off on celite, and the mother liquor was concentrated in vacuo. The residual solid was washed with diethyl ether under stirring, the solid was collected by filtration to obtain the titled compound (872 mg) as a colorless powder.

Workup

  1. temperaturethe suspension was heated
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationthe catalyst was filtered off on celite
  4. concentrationthe mother liquor was concentrated in vacuo
  5. washThe residual solid was washed with diethyl ether
  6. stirringunder stirring
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-6386e7ba5ed64971bb681f1605fecbd3
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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