Ethyl 2-nitro-4-benzoylphenylacetate → Ethyl 2-amino-4-benzoylphenylacetate

HRID 236372

Reaction equation

HRID 236372 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([O-])=O>[Ni].C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 1

HCID 13770535Ethyl 2-nitro-4-benzoylphenylacetate

Product 1

HCID 13770537Ethyl 2-amino-4-benzoylphenylacetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 14 g. (44.7 mmoles) of ethyl 2-nitro-4-benzoylphenylacetate in 225 ml. of ethanol was added 15 g. of wet Raney nickel and the mixture heated to reflux for 1.5 hours. The mixture was filtered and the filtrate concentrated to give a residual oil which was induced to crystallize by trituration with diethyl ether, 7.9 g., m.p. 150°-152° C.

Workup

  1. temperatureto reflux for 1.5 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customto give a residual oil which
  5. customto crystallize by trituration with diethyl ether, 7.9 g

Sources & evidence

ORD record
ord-1236173910b142118fc888e02d448121
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Linked notes

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