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

HRID 371761Notes

Reaction equation

HRID 371761 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-739b61f659d247319956cde1ac419e8b
Source dataset
uspto-grants-1978_05
Patent number
US04087606

Reaction notes

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