Sodium Carbonate → HCID 13812588, compound

HRID 344687Notes

Reaction equation

HRID 344687 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:10][C:11](=[N:13]O)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:12][C:11]1[N:13]=[C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[O:8][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67180Acetone, oximeHCID 82604Nicotinoyl chloride

Product 1

HCID 13812588HCID 13812588, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

30 g of nicotinoyl chloride is added to 5.1 g of cooled acetoxime, then the mixture is heated to 130° C. The exothermic reaction mixture is maintained under agitation for 6 hours at 140° C. After cooling, iced water is added, followed by alkalizing with sodium carbonate and extracting with methylene chloride. The solvent is evaporated, the residue is taken up with ether and filtered; the solvent is evaporated and the residue is distilled at 150° C. under 0.08 mbar. 3.5 g of expected product is obtained which is purified by chromatography on silica (eluant: cyclohexane-ethyl acetate 7-3), with further distillation. After cooling, a solid product is obtained.

Workup

  1. temperatureThe exothermic reaction mixture is maintained under agitation for 6 hours at 140° C
  2. temperatureAfter cooling
  3. extractionextracting with methylene chloride
  4. customThe solvent is evaporated
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. distillationthe residue is distilled at 150° C. under 0.08 mbar

Sources & evidence

ORD record
ord-52e68653cbd7473cbd369cf924079ffe
Source dataset
uspto-grants-1991_10
Patent number
US05053416

Reaction notes

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