Pyridine → HCID 70588340, compound

HRID 2057808Notes

Reaction equation

HRID 2057808 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][OH:10])[C:5]([CH2:11][Cl:12])=[CH:4][N:3]=1.C(Cl)(Cl)Cl.N1C=CC=CC=1.[C:23](Cl)(Cl)=[O:24]>C1C=CC=CC=1>[Cl:12][CH2:11][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[C:7]2[O:8][C:23](=[O:24])[O:10][CH2:9][C:6]=12

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 6371PhosgeneHCID 2031304-Pyridinemethanol, 5-chloromethyl-3-hydroxy-2-methyl-

Product 1

HCID 70588340HCID 70588340, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 0.01 mole of 2-methyl-3-hydroxy-4-hydroxymethyl-5-chloromethylpyridine in 50 ml. chloroform and 50 ml. pyridine is added at 0°-5° C. a solution of 0.011 moles of phosgene in benzene. The reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is then concentrated in vacuo and excess saturated sodium bicarbonate solution is added. The resulting solid is collected by filtration. Chromatography on silica gel and elution with methanol in chloroform (1-5%) gives 5-chloromethyl-8-methyl-2-oxo-4H-m-dioxino[4,5-c]pyridine.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo and excess saturated sodium bicarbonate solution
  2. additionis added
  3. filtrationThe resulting solid is collected by filtration
  4. washChromatography on silica gel and elution with methanol in chloroform (1-5%)

Sources & evidence

ORD record
ord-d65a4e04168343d28d30f924be84b361
Source dataset
uspto-grants-1980_07
Patent number
US04212976

Reaction notes

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