Ethyl 5-aminocarbonyl-4,6-diethoxy-2-(trifluoromethyl)-3-pyridinecarboxylate → Ethyl 5-cyano-4,6-diethoxy-2-(trifluoromethyl)-3-pyridinecarboxylate

HRID 64571Notes

Reaction equation

HRID 64571 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([O:22][CH2:23][CH3:24])=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]([C:13]([F:16])([F:15])[F:14])=[N:8][C:9]=1[O:10][CH2:11][CH3:12])=O>O=P(Cl)(Cl)Cl>[C:2]([C:4]1[C:5]([O:22][CH2:23][CH3:24])=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]([C:13]([F:16])([F:14])[F:15])=[N:8][C:9]=1[O:10][CH2:11][CH3:12])#[N:1]

Participants

3

Reactant 1

HCID 13726805Ethyl 5-aminocarbonyl-4,6-diethoxy-2-(trifluoromethyl)-3-pyridinecarboxylate

Product 1

HCID 13726806Ethyl 5-cyano-4,6-diethoxy-2-(trifluoromethyl)-3-pyridinecarboxylateYield 24.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 6.17 g (0.018 mol) of product of Example 23 and 100 ml of POCl3 was held at reflux for 7 hours and concentrated in vacuo. The residue was poured into water and extracted with ether. The ether extract was washed with 15% K2CO3, dried (MgSO4) and concentrated to give 1.44 g (24.6%) of product as an oil; nD25 1.4677.

Workup

  1. temperatureat reflux for 7 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was poured into water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with 15% K2CO3
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0a5ba215e4d54f62a36cd7a1395a13e7
Source dataset
uspto-grants-1986_09
Patent number
US04609399

Reaction notes

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