Acetic Acid → HCID 18680895, compound

HRID 276059Notes

Reaction equation

HRID 276059 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:23])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=O)[CH3:18])=[C:12]([N+:20]([O-])=O)[CH:11]=1.C(O)(=O)C.[H][H]>[Pd].C(O)C>[CH3:18][C:17]1[NH:20][C:12]2[CH:11]=[C:10]([C:9](=[O:23])[NH:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:15]=[CH:14][C:13]=2[N:16]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 18680988HCID 18680988, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18680895HCID 18680895, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Five-percent palladium on carbon (0.10 g) was added to a mixture of 1.00 g of crude N-(2-pyridylmethyl)-4-acetylamino-3-nitrobenzamide, 8 ml of acetic acid and 12 ml of ethanol, and the solution was stirred in a hydrogen atmosphere at 80° C. for 7 hours. The solid material was separated through filtration, and the filtrate was concentrated. Ethyl acetate was added to the residue for crystallization. The crystals were separated through filtration, and were dried to give 0.57 g of 2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (252).

Workup

  1. customThe solid material was separated through filtration
  2. concentrationthe filtrate was concentrated
  3. additionEthyl acetate was added to the residue for crystallization
  4. customThe crystals were separated through filtration
  5. customwere dried

Sources & evidence

ORD record
ord-61c2d8c697164f778cfbe22c32e4a24d
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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