Benzyl Chloride → 3-Benzyloxy-1-carboxymethylpyrid2-one

HRID 1906174Notes

Reaction equation

HRID 1906174 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[C:8]1=[O:14])=[O:5])C.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>CO.O>[CH2:15]([O:13][C:9]1[C:8](=[O:14])[N:7]([CH2:6][C:4]([OH:3])=[O:5])[CH:12]=[CH:11][CH:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 11127212ethyl 2-(3-hydroxy-2-oxopyridin-1(2H)-yl)acetate2×

Product 1

HCID 133367273-Benzyloxy-1-carboxymethylpyrid2-oneYield 41%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

1-Ethoxycarbonylmethyl-3-hydroxypyrid-2-one (10 g), prepared as described under (B), is dissolved in methanol/water (9:1 v/v) (400 ml). To this solution is added benzyl chloride (3 molar excess) and NaOH until the pH is above 12. The mixture is then refluxed for six hours to give a clear orange solution. The methanol is removed by rotary evaporation and the aqueous solution is extracted with dichloromethane to remove excess benzyl chloride. The aqueous phase is diluted slightly by adding extra water and then acidified to pH 2 using concentrated hydrochloric acid which results in the precipitation of a beige solid. The mixture is cooled and the precipitate filtered off and washed with diethyl ether. The crude product is recrystallised from ethanol to give 3-benzyloxy-1-carboxymethylpyrid-2-one (5.4 g, 41%), m.p. 176°-177° C.

Workup

  1. temperatureThe mixture is then refluxed for six hours
  2. customto give a clear orange solution
  3. customThe methanol is removed by rotary evaporation
  4. extractionthe aqueous solution is extracted with dichloromethane
  5. customto remove excess benzyl chloride
  6. additionThe aqueous phase is diluted slightly
  7. additionby adding extra water
  8. customresults in the precipitation of a beige solid
  9. temperatureThe mixture is cooled
  10. filtrationthe precipitate filtered off
  11. washwashed with diethyl ether
  12. customThe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-08ec92e9433b4732b9ebed02332877af
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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