Acetyl chloride → HCID 18960874, compound

HRID 257452Notes

Reaction equation

HRID 257452 reaction equation
[N+:1]([CH2:4][CH2:5][CH3:6])([O-:3])=O.C[O-].[Na+].[C:10](Cl)(=O)[CH3:11].C([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)#C>CC(N(C)C)=O.O>[CH2:5]([C:4]1[CH:19]=[C:20]([C:21]2[CH:16]=[N:17][CH:18]=[CH:10][CH:11]=2)[O:3][N:1]=1)[CH3:6]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 79031-NitropropaneHCID 137268EthynylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 18960874HCID 18960874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

0.45 g (5 mmole) nitropropane and 5 ml 1N (5 mmole) sodiummethoxide was dissolved in dry dimethylacetamide (25 ml). To this solution 0.39 g (5 mmole) acetylchloride and 0.51 g (5 mmole) 2-ethynylpyridine was added. The reaction mixture was stirred overnight at room temperature. Water (150 ml) was added, and the solution extracted with 3×30 ml ethylacetate. The organic phase was dried over magnesiumsulphate and concentrated in vacuo giving 3-(3-ethyl-5-isoxazolyl)pyridine in a 500 mg yield. This compound was quartarnized with methyliodide and reduced with sodiumborohydride as described above giving the title compound in a 170 mg yield. M.p. 169°-170° C.

Workup

  1. extractionthe solution extracted with 3×30 ml ethylacetate
  2. dry with materialThe organic phase was dried over magnesiumsulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1eb9354a93944c7890689af9b4b7cc0a
Source dataset
uspto-grants-1993_11
Patent number
US05262427

Reaction notes

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