Hydrochloric Acid → HCID 21510394, compound

HRID 1576958Notes

Reaction equation

HRID 1576958 reaction equation
Cl.C([O:5][C:6]1[C:7]([CH3:14])=[N:8][CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1)(=O)C.Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.N1C=CC=CC=1>[OH:5][C:6]1[C:7]([CH3:14])=[N:8][CH:9]=[C:10]([CH2:12][O:13][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 21510395HCID 21510395, compound

Product 1

HCID 21510394HCID 21510394, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.4 g. of 3-acetoxy-5-hydroxymethyl-2-methylpyridine hydrochloride in 20 ml. of pyridine was added a solution of 2.0 g. of isonicotinoyl chloride hydrochloride in 15 ml. of dimethylformamide under cooling and the resulting mixture was stirred at room temperature for 16 hours. Then, the reaction mixture was poured into ice-water and the mixture was extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off to give an oily substance. The substance was taken into 25 ml. of 2N HCl and the resulting mixture was stirred at 80°C. for 30 minutes. The mixture was neutralized with sodium bicarbonate, filtered and recrystallized from methanol to give 0.9 g. of the desired product. m. p. 180° - 180.5°C.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customto give an oily substance
  6. filtrationfiltered
  7. customrecrystallized from methanol
  8. customto give 0.9 g

Sources & evidence

ORD record
ord-81109d3ff96e47af97d9465a6f944caa
Source dataset
uspto-grants-1976_09
Patent number
US03983238

Reaction notes

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