2(5H)-Furanone, 5-hydroxy-4-methyl- → ethyl [4-methyl-6-oxopyridazin-1(6H)-yl]acetate

HRID 887110Notes

Reaction equation

HRID 887110 reaction equation
O[CH:2]1O[C:5](=[O:7])[CH:4]=[C:3]1[CH3:8].Cl.[NH:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH2:11]>C(O)C>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][N:10]1[C:5](=[O:7])[CH:4]=[C:3]([CH3:8])[CH:2]=[N:11]1)[CH3:17]

Participants

4

Reactant 2

HCID 1153012(5H)-Furanone, 5-hydroxy-4-methyl-HCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 77231410ethyl [4-methyl-6-oxopyridazin-1(6H)-yl]acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Hydroxy-4-methylfuran-2(5H)-one (1.19 g, 10.4 mmol) and ethyl hydrazinoacetate hydrochloride (1.61 g, 10.4 mmol) in 95% ethanol (20 mL) was refluxed for 2 h. Removal of the solvent in vacuo followed by purification using a Biotage Horizon® system (0-50% ethyl acetate/hexanes mixture) gave ethyl[4-methyl-6-oxopyridazin-1(6H)-yl]acetate as a yellow crystalline. LC/MS 219.2 (M+23).

Workup

  1. customRemoval of the solvent in vacuo
  2. customfollowed by purification

Sources & evidence

ORD record
ord-8e4e4931067848af9008f593bf1ade5b
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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