2-Benzofurancarboxylic acid, 5-nitro-, ethyl ester → Ethyl 5-aminobenzofuran-2-carboxylate

HRID 1169

Reaction equation

HRID 1169 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:8]=2[CH:17]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:8]=2[CH:17]=1

Participants

4

Reactant 1

HCID 13829542-Benzofurancarboxylic acid, 5-nitro-, ethyl ester

Product 1

HCID 9837138Ethyl 5-aminobenzofuran-2-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.3 g of ethyl 5-nitrobenzofuran-2-carboxylate in 60 ml of methanol is hydrogenated in the presence of Raney nickel. The catalyst is filtered off and the solution is concentrated. After customary working up, ethyl 5-aminobenzofuran-2-carboxylate, Rf 0.1 (dichloromethane/ethanol 9.5:0.5) obtained; hydrochloride m.p. 246°-248°.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-fb1ddf8127a44d35bcac2a8bffbfe5d1
Source dataset
uspto-grants-1998_03
Patent number
US05723614

Linked notes

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