Nitromethane → (3-Methylisoxazole-5-yl)glyoxal-2-oxim

HRID 1389259Notes

Reaction equation

HRID 1389259 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]=[O:8])[O:4][N:3]=1.[N+:9]([CH3:12])([O-])=[O:10].[O-]CC.[Na+].[Na]>C(O)C.CCOCC>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([CH:12]=[N:9][OH:10])=[O:8])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 105827583-Methyl-1,2-oxazole-5-carbaldehyde

Product 1

HCID 88761968(3-Methylisoxazole-5-yl)glyoxal-2-oximYield 70.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

In 50 ml of ethanol were dissolved 5.5 g of 3-methylisoxazole-5-carbaldehyde and 3.3 g of nitromethane. To the solution was added dropwise a solution of sodium ethoxide in ethanol, which had been prepared from 1.5 g of sodium and 30 ml of ethanol, while stirring at room temperature. After completion of the dropwise addition, the resultant solution was stirred for a further 3 hrs. at room temperature and then ether was added thereto to separate the sodium salt. This was dissolved in water, which was followed by acidification with hydrochloric acid. The resulting precipitate was filtered off and recrystallized from chloroform to obtain 5.4 g of (3-methylisoxazole-5-yl)glyoxal-2-oxim having m.p. of 179° C.-180° C. Yield, 70%.

Workup

  1. additionAfter completion of the dropwise addition
  2. customto separate the sodium salt
  3. dissolutionThis was dissolved in water
  4. filtrationThe resulting precipitate was filtered off
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-7bf5ffd5eb9c46a6b06846330667a66f
Source dataset
uspto-grants-1981_01
Patent number
US04243812

Reaction notes

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