Methyl iodide → HCID 23206014, compound

HRID 1741631Notes

Reaction equation

HRID 1741631 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9][C:10]=1[CH3:11])(=[O:3])[CH3:2].[H-].[Na+].[CH3:24]I>O1CCCC1>[CH3:11][C:10]1[N:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][C:5]=1[N:4]([CH3:24])[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21847058HCID 21847058, compound

Product 1

HCID 23206014HCID 23206014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2.94 g of 5-acetamido-6-methylpyridine-2,3-dicarboxylic acid, diethyl ester, and 0.44 g of 60% sodium hydride in 200 mL dry tetrahydrofuran is kept at room temperature for 1 hour, then 0.93 mL of methyl iodide is added, and the reaction is stirred for an additional 4 hours. The reaction is concentrated in vacuo, and the residue is slurried in water, the pH is adjusted to 3 with hydrochloric acid, and the mixture is extracted with methylenechloride. The organic phase is dried, concentrated in vacuo to afford the desired product as an oil.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. extractionthe mixture is extracted with methylenechloride
  3. customThe organic phase is dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d0729b2eb28461eb6f0a9575d98bb57
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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