Hydrogen chloride-ethyl acetate → HCID 67399142, compound

HRID 1426684Notes

Reaction equation

HRID 1426684 reaction equation
[C:1]([CH:3]([CH:9]([CH3:19])[C:10]([C:12]1[C:13]([F:18])=[N:14][CH:15]=[CH:16][CH:17]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(OCC)(=O)C.[ClH:26]>C(OCC)(=O)C>[Cl:26][C:1]1[NH:2][C:10]([C:12]2[C:13]([F:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([CH3:19])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 59826886HCID 59826886, compound

Product 1

HCID 67399142HCID 67399142, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-cyano-4-(2-fluoropyridin-3-yl)-3-methyl-4-oxobutanoate (19.4 g) in ethyl acetate (20 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (90 mL), and the mixture was stirred for 18 hr, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound as yellow crystals (yield 14.3 g, 69%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-db73606ff3d94b87980c455da5f7df4b
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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