Propionitrile → 2-Methyl-3-oxo-3-(4-(trifluoromethyl)phenyl)propionitrile

HRID 1695182

Reaction equation

HRID 1695182 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5]NN=1.CO[C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.[H-].[Na+].C(#N)CC>>[CH3:5][CH:6]([C:9](=[O:20])[C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)[C:2]#[N:1]

Participants

5

Reactant 4

HCID 7854PropionitrileHCID 24758Sodium hydrideHCID 520447Methyl 4-(trifluoromethyl)benzoateHCID 178418806HCID 178418806, compound

Product 1

HCID 431572662-Methyl-3-oxo-3-(4-(trifluoromethyl)phenyl)propionitrileYield 96%

Procedure

The product was prepared according to the general procedure for aminopyrazole synthesis (route A1) from 4-trifluoromethyl-benzoic acid methyl ester (3.0 g, 14.7 mmol, 1.0 eq), NaH (1.2 g, 29.4 mmol, 2.0 eq) and propionitrile (4.9 mL, 69.4 mmol, 4.7 eq). The crude product was extracted with DCM and used in the following step without further purification (3.2 g, yield: 96%).

Workup

  1. customThe product was prepared
  2. extractionThe crude product was extracted with DCM
  3. customused in the following step without further purification (3.2 g, yield: 96%)

Sources & evidence

ORD record
ord-bd720de13d4141079f412edd57df2be6
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Linked notes

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