Acetic Acid → ethyl 2-methyl-1H-benzimidazole-4-carboxylate

HRID 276067Notes

Reaction equation

HRID 276067 reaction equation
[C:1]([NH:4][C:5]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=O)[CH3:2].[C:18](O)(=O)C>C(O)C>[CH2:10]([O:9][C:7]([C:6]1[C:5]2[NH:4][C:1]([CH3:2])=[N:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)=[O:8])[CH3:18]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 2782278Methyl 2-acetamido-3-nitrobenzoate

Product 1

HCID 18680979ethyl 2-methyl-1H-benzimidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.03 g of methyl 2-acetylamino-3-nitrobenzoate, 18.8 g of reduced iron, 20 ml of acetic acid and 40 ml of ethanol was heat-refluxed for 18 hours. After the solvent was concentrated, chloroform and 10% hydrochloric acid were added to the residue for extraction. The aqueous layer was acidified with a saturated aqueous solution of sodium hydrogencarbonate, and was extracted with chloroform. Chloroform was then distilled off under reduced pressure to give 1.61 g of 4-ethoxycarbonyl-2-methylbenzimidazole (296).

Workup

  1. temperaturewas heat-refluxed for 18 hours
  2. concentrationAfter the solvent was concentrated
  3. additionchloroform and 10% hydrochloric acid were added to the residue for extraction
  4. extractionwas extracted with chloroform
  5. distillationChloroform was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-d53c57b0a8a74d8db5bf038f7e098867
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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