Sodium Hydroxide → HCID 86746208, compound

HRID 466475Notes

Reaction equation

HRID 466475 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([CH:14]([F:16])[F:15])[C:5]=1[C:17]([O:19][CH3:20])=[O:18].[OH-:22].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:8]([C:9](=[C:4]1[CH:5]([CH3:17])[CH2:6][CH2:14][O:22]1)[C:9]1[C:4]([CH2:3][CH:2]([CH3:21])[CH3:1])=[C:5]([C:17]([O:19][CH3:20])=[O:18])[C:6]([CH:14]([F:16])[F:15])=[N:7][C:8]=1[C:10]([F:12])([F:13])[F:11])#[N:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57222561HCID 57222561, compound

Product 1

HCID 86746208HCID 86746208, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g (14.3 mmol) of 5-(cyanomethyl)-4-(2-methylpropyl-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example d, above, 5.0 g (34.9 mmol) 1-methyl-4-chlorobutyryl chloride, 0.37 g benzyltriethylammonium chloride, and 150 mL dichloromethane was added 82 mL 50% NaOH. The solution was stirred at room temperature for 2 hours. The reaction was then quenched with ice water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered through silica gel and concentrated to give 5.2 g of crude product. Purification by chromatography using 20% ethyl acetate in hexanes yielded 3.1 g of the desired product as a yellow oil, a 51% yield. nD25 1.4887.

Workup

  1. customThe reaction was then quenched with ice water
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered through silica gel
  5. concentrationconcentrated
  6. customto give 5.2 g of crude product
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-f57ca2ec7fb04ccaaff246f3207cac04
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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