Water → HCID 21942481, compound

HRID 2216743Notes

Reaction equation

HRID 2216743 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=1.I[CH3:21].O>CN(C)C=O>[CH3:21][O:3][C:4]1[CH:5]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178469316HCID 178469316, compound

Product 1

HCID 21942481HCID 21942481, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.351 g, 8.77 mmol) in dimethylformamide (7.5 mL), a solution of diethyl 4-hydroxy-2,6-pyridinedicarboxylate (1.4 g, 5.85 mmol) in dimethylformamide (9 mL) was added dropwise under argon at room temperature and the reaction mixture was stirred for 5 minutes. Iodomethane (1.245 g, 8.77 mmol) was added and the reaction was stirred at room temperature for 20 hours. The mixture was poured into water and extracted with dichloromethane. The dichloromethane layer was dried, concentrated to give 1.45 g (97.8%) diethyl 4-methoxy-2,6-pyridinedicarboxylate.

Workup

  1. stirringthe reaction was stirred at room temperature for 20 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe dichloromethane layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb0ae6d46e424a8c9baf4aeac227819c
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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