Cyclohexene → Ethyl 2-[(3-amino-2-cyanophenyl)amino]-2-oxoacetate

HRID 972964Notes

Reaction equation

HRID 972964 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:9]=1[C:17]#[N:18])=[O:6])[CH3:2].C1CCCCC=1>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:9]=1[C:17]#[N:18])=[O:6])[CH3:2]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 12715758HCID 12715758, compound

Product 1

HCID 12715740Ethyl 2-[(3-amino-2-cyanophenyl)amino]-2-oxoacetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound is prepared by reduction of [3-nitro-2-cyanophenylamino]oxoacetic acid ethyl ester with 10% Pd. on charcoal and with cyclohexene in ethanol according to the procedure of I. D. Entwistle and R. A. W. Johnstone, J. Chem. Soc., Perkin I. 1300 (1975). The crude product is chromatographed on silica gel with chloroform and recrystallized from ethanol, m.p. 133°-136° C.

Workup

  1. customThe crude product is chromatographed on silica gel with chloroform
  2. customrecrystallized from ethanol, m.p. 133°-136° C.

Sources & evidence

ORD record
ord-0db0fc8397e54c9485d0e0d7ea338c79
Source dataset
uspto-grants-1977_10
Patent number
US04054591

Reaction notes

Loading…