Methyl iodide → 4-Methoxy-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

HRID 2291458Notes

Reaction equation

HRID 2291458 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:14])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F:20][C:2]([F:19])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH3:21])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178470034HCID 178470034, compound

Product 1

HCID 138828664-Methoxy-2,6-bis-trifluoromethyl-nicotinic acid ethyl esterYield 83.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.0 g (0.026 mol) of product of Example 2, 3.6 g (0.026 mol) of potassium carbonate, g of methyl iodide, and 50 ml of acetone was held at reflux for 6 hours and concentrated. The residue was treated with water and extracted with ether. The ether extract was washed once with 30 ml of 10% NaOH, dried, and concentrated. The residue was crystallized from hexane to give 6.91 g (82.5%) of product; mp 58.5°-59.5° C.

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationconcentrated
  3. additionThe residue was treated with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed once with 30 ml of 10% NaOH
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-fa7da22472c34b1280e3612fa812d1e3
Source dataset
uspto-grants-1989_01
Patent number
US04797149

Reaction notes

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