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

HRID 1707015Notes

Reaction equation

HRID 1707015 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-15b1fa89360848bbbdc40e5ab879f972
Source dataset
uspto-grants-1980_06
Patent number
US04209523

Reaction notes

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