Methyl iodide → Ethyl 2-methoxy-6-methylisonicotinate

HRID 249731Notes

Reaction equation

HRID 249731 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:14]I>C1(C)C=CC=CC=1>[CH3:14][O:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178469038HCID 178469038, compound

Product 1

HCID 45076200Ethyl 2-methoxy-6-methylisonicotinateYield 77.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

20.0 g (111.4 mmol) of ethyl 2-hydroxy-6-methylisonicotinate (20a) were suspended in 330 ml of toluene. After addition of 36.54 g (132.5 mmol) of Ag2CO3 and 23.5 g (165.6 mmol) of methyl iodide, the mixture was heated to 100° C. with KPG stirring. After 4 hours, the reaction mixture was allowed to cool to RT and it was filtered through Celite. The filtrate was washed twice with water, dried with Na2SO4 and concentrated, 16.9 g of the title compound being isolated as a yellowish oil.

Workup

  1. temperatureto cool to RT
  2. filtrationit was filtered through Celite
  3. washThe filtrate was washed twice with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fda1b12a7fe14a0dbd517374718a985e
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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