Pyridine → HCID 70588340, compound

HRID 918574Notes

Reaction equation

HRID 918574 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-5253bb7a488e4560b2aad32c52742335
Source dataset
uspto-grants-1976_07
Patent number
US03971797

Reaction notes

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