Ethyl 2-[(4-nitrobenzoyl)amino]acetate → Ethyl 4-aminobenzamidoacetate

HRID 26805Notes

Reaction equation

HRID 26805 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 345309Ethyl 2-[(4-nitrobenzoyl)amino]acetate

Product 1

HCID 12469740Ethyl 4-aminobenzamidoacetateYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

17.6 g (0.07 mol) of ethyl 4-nitro-benzamidoacetate dissolved in 250 ml of ethanol are hydrogenated in the presence of a catalyst (2 g of palladium on charcoal); the catalyst is filtered off, the filtrate is evaporated to dryness in vacuo, the residue is taken up in 100 ml of diisopropyl ether and the product is filtered off. 15 g (87% yield) of the stated product are obtained. Melting point: 93°-94° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness in vacuo
  3. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-a37f93afba1847539f06263056a9de88
Source dataset
uspto-grants-1979_04
Patent number
US04151300

Reaction notes

Loading…