Hydrochloric Acid → (3-Methylisoxazole-5-yl)glyoxal-2-oxim

HRID 1389260Notes

Reaction equation

HRID 1389260 reaction equation
[C:1]([C:4]1[O:8][N:7]=[C:6]([CH3:9])[CH:5]=1)(=[O:3])[CH3:2].Cl.[N:11](OCCCCC)=[O:12]>CCOCC>[CH3:9][C:6]1[CH:5]=[C:4]([C:1]([CH:2]=[N:11][OH:12])=[O:3])[O:8][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10026Pentyl nitriteHCID 130013941-(3-Methyl-1,2-oxazol-5-yl)ethan-1-one

Product 1

HCID 88761968(3-Methylisoxazole-5-yl)glyoxal-2-oximYield 32.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 30 ml of ether was dissolved 2.5 g of 5-acetyl-3-methylisoxazole. While gaseous hydrogen chloride was passed through the resultant solution with stirring, a solution of 4.5 g of amyl nitrite in 10 ml of ether was dropped thereinto. After a further one hour stirring at room temperature after completion of said dropwise addition, the resulting precipitate was isolated by filtration. Recrystallization from chloroform gave 1.0 g of (3-methylisoxazole-5-yl)glyoxal-2-oxim having m.p. of 179° C.-180° C. Yield, 27%.

Workup

  1. stirringAfter a further one hour stirring at room temperature after completion
  2. additionaddition
  3. customthe resulting precipitate was isolated by filtration
  4. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-a17c8fcfd5d34d1cbafd9c0078599c54
Source dataset
uspto-grants-1981_01
Patent number
US04243812

Reaction notes

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