2,6-Lutidine → Ethyl 2,6-bis(trifluoromethyl)-4-chloro-5-methyl-3-pyridinecarboxylate

HRID 542137Notes

Reaction equation

HRID 542137 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7](O)[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1.N1C(C)=CC=CC=1C.P(Cl)(Cl)([Cl:32])=O>>[F:1][C:2]([F:21])([F:20])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([Cl:32])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 178469144HCID 178469144, compound

Product 1

HCID 13882926Ethyl 2,6-bis(trifluoromethyl)-4-chloro-5-methyl-3-pyridinecarboxylateYield 57.8%

Procedure

A mixture of 5.0 g (0.016 mol) of product of Example 35, 4.52 g (0.0362 mol) of 2,6-lutidine and 34 ml of phosphorus oxychloride was held at reflux for 20 hours and concentrated in vacuo. The residue was quenched with water and extracted with ether. The ether extract was washed successively with 10% K2CO3 and water, dried (CaSO4) and concentrated in vacuo to give 3.06 g (57.8%) of product as a brown oil, nD25 1.4313.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was quenched with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed successively with 10% K2CO3 and water
  7. dry with materialdried (CaSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-183e86b95bd54a278e491c0e953abdbb
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

Loading…