Isoniazid → Ethyl Valerate Isonicotinoylhydrazone

HRID 1742101Notes

Reaction equation

HRID 1742101 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.[C:12](=N)([O:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH2:15][CH3:16]>C(O)C>[C:1]([NH:9][N:10]=[C:12]([O:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH2:15][CH3:16])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 12283341Ethyl pentanimidate hydrochloride

Product 1

HCID 54521080Ethyl Valerate IsonicotinoylhydrazoneYield 51.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture of 2.46 g (17.9 mmole) of isonicotinic hydrazide and 50 ml of ethanol was stirred at -10° C. as a solution of 2.52 g (16.6 mmole) of ethyl valerimidate hydrochloride, in 46 ml of ethanol was added dropwise under protection from moisture. The mixture was maintained at -10° C. for three hours and then at 5° C. overnight. The filtered solution was concentrated, and the residue was flash chromatographed on silica gel (elution with 2.5% methanol in CH2Cl2) to provide 2.12 g (50%) of the titled compound as an oil which goes to a waxy solid at 5° C., homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 250 (M+1)+. NMR suggested that the product is a mixture of syn and anti-isomers.

Workup

  1. additionwas added dropwise under protection from moisture
  2. customat 5° C.
  3. customovernight
  4. concentrationThe filtered solution was concentrated
  5. customchromatographed on silica gel (elution with 2.5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-75a4bb74c4e2412dab74eab5990cd104
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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