HCID 18680988, compound → HCID 18315403, compound

HRID 276019Notes

Reaction equation

HRID 276019 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:19])[CH3:18])=[C:12]([N+:20]([O-])=O)[CH:11]=1.[H][H]>[Pd].CO>[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:19])[CH3:18])=[C:12]([NH2:20])[CH:11]=1

Participants

5

Reactant 2

HCID 18680988HCID 18680988, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18315403HCID 18315403, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Five-percent palladium on carbon (2.53 g) was added to a solution of 10.0 g of N-(2-pyridylmethyl)-4-acetylamino-3-nitrobenzamide in 150 ml of methanol, and the mixture was stirred in a hydrogen atmosphere at 60° C. for 15 hours. The solid material was separated through filtration, and the filtrate was concentrated. The resulting residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 7:3) to give 8.02 g of N-(2-pyridylmethyl)-4-acetylamino-3-aminobenzamide.

Workup

  1. customThe solid material was separated through filtration
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified through silica-gel column chromatography (eluent
  4. additiona mixture of ethyl acetate and methanol at a ratio of 7:3)

Sources & evidence

ORD record
ord-79b1e83c41cc4f62b15f15aa84441728
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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