Hydrochloric Acid → 5-Ethyl 3-methyl 6-(difluoromethyl)-4-(isopropylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 255434Notes

Reaction equation

HRID 255434 reaction equation
[F:1][CH:2]([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([NH:17][CH:18]([CH3:20])[CH3:19])[C:4]=1[C:21]([O:23][CH3:24])=[O:22].[OH-].[K+].Cl.[C:29]([O-])([O-])=O.[K+].[K+].C(I)C>CN(C=O)C.O>[F:25][CH:2]([F:1])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([NH:17][CH:18]([CH3:20])[CH3:19])[C:4]=1[C:21]([O:23][CH2:24][CH3:29])=[O:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 14013774Dimethyl 6-(difluoromethyl)-4-(iso propylamino)-2-(trifluoromethyl)-3,5-pyridine-dicarboxylate

Product 1

HCID 140138205-Ethyl 3-methyl 6-(difluoromethyl)-4-(isopropylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 775.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.1 g (0.001 mol) of product of Example 76, 0.62 g (0.011 mol) of KOH and 5 ml of H2O overnight. The reaction mixture was poured into 250 ml of H2O containing 50 ml of concentrated HCl, extracted with ether, dried (mgSO4) and concentrated in vacuo to 3.76 g of yellow air. This oil, 152 g (0.011 mol) of K2CO3 and 0.88 ml (0.011 mol) of ethyl iodide in 30 ml of DMF was stirred at room temperature overnight. The reaction mixture was poured into water extracted with ether, drid (MgSO4) and concentrated in vacuo to 3.64 g of yellow oil. Kugelrohr distillation at 53 Pa, pot temperature 103° C., afforded 2.98 g (70.5%) of product sa a light yellow oil which solidified; mp 37°-39° C.

Workup

  1. extractionextracted with ether
  2. customdried (mgSO4)
  3. concentrationconcentrated in vacuo to 3.76 g of yellow air
  4. extractionextracted with ether
  5. concentrationconcentrated in vacuo to 3.64 g of yellow oil
  6. distillationKugelrohr distillation at 53 Pa, pot temperature 103° C.

Sources & evidence

ORD record
ord-4c69d8c06b17479a8ddebe5a4d38deab
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Reaction notes

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