Sodium Hydroxide → HCID 131717579, compound

HRID 466477Notes

Reaction equation

HRID 466477 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH3:21])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])#[N:2].Cl[CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27].[OH-].[Na+]>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([C:3](=[C:26]1[CH2:25][CH2:24][CH2:23][O:27]1)[C:4]1[C:5]([CH3:21])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:12])([F:13])[F:11])#[N:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 131717580HCID 131717580, compound

Product 1

HCID 131717579HCID 131717579, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.00 g (22.7 mmol) 5-(cyanomethyl)-2-(difluoromethyl)-4-methyl-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example E, in 450 mL dichloromethane was added 6.41 g (45.4 mmol) 4-chlorobutyryl chloride, 0.30 g benzyltriethylammonium chloride, and 135 mL 50% sodium hydroxide. The mixture was stirred for 30 minutes, poured over ice, and extracted with diethyl ether. The organic layer was dried with magnesium sulfate, treated wit decolorizing carbon, filtered through silica gel, and evaporated in vacuo. The residue was recrystallized in ethyl acetate and hexane, yielding 4.59 g of the desired product as a white crystalline solid, a 54% yield. m.p. 160°-161° C.

Workup

  1. additionpoured over ice
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. additiontreated wit
  5. filtrationfiltered through silica gel
  6. customevaporated in vacuo
  7. customThe residue was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-c08be83fb37b4174bfd652cf410c0eb4
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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