N-benzyl-3-nitrobenzamide → 3-amino-N-benzylbenzamide

HRID 609575Notes

Reaction equation

HRID 609575 reaction equation
[C:1]1([CH2:7][NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[C:1]1([CH2:7][NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 347075N-benzyl-3-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 41998383-amino-N-benzylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of the product of step (a), 8.8 g, was dissolved in 100 ml of methanol and hydrogenated with 0.4 g of 10% palladium on carbon and 50 PSI hydrogen. After 90 minutes, the mix was filtered and evaporated. The solid residue was slurried in ethyl ether, and filtered to provide crude N-phenylmethyl-3-aminobenzamide, mp 95-100° C, m.s. (M+H)+ =227

Workup

  1. filtrationthe mix was filtered
  2. customevaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-06a9e500ffbf42d2b1e976035826e0c8
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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