alpha-Formyl-3-(trifluoromethyl)benzeneacetonitrile → 3-Amino-2-[3-(trifluoromethyl)phenyl]-2-propenal

HRID 1707098Notes

Reaction equation

HRID 1707098 reaction equation
[CH:1]([CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[C:4]#[N:5])=[O:2]>C(O)C>[NH2:5][CH:4]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=1)[CH:1]=[O:2]

Participants

3

Reactant 1

HCID 13133052alpha-Formyl-3-(trifluoromethyl)benzeneacetonitrile

Product 1

HCID 867370753-Amino-2-[3-(trifluoromethyl)phenyl]-2-propenal

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

portions of α-formyl-3-(trifluoromethyl)benzeneacetonitrile each in 250 ml. of ethanol are hydrogenated in the presence of 40 g. of Raney Nickel (number 28) at 20 psi pressure until no more hydrogen is absorbed. The resulting mixtures are filtered and the filtrates are combined and passed through 150 g. of alumina (Woelm, activity II) with 1:1 methylene chloride-ethyl acetate. The resulting eluate is concentrated at reduced pressure and the residue triturated with hexane to give 39.4 g. of the product of the Example as a yellow solid, m.p. 63°-70° C.

Workup

  1. customof Raney Nickel (number 28) at 20 psi pressure until no more hydrogen is absorbed
  2. filtrationThe resulting mixtures are filtered
  3. concentrationThe resulting eluate is concentrated at reduced pressure
  4. customthe residue triturated with hexane
  5. customto give 39.4 g

Sources & evidence

ORD record
ord-a0b607016deb4462b480570ecaff0462
Source dataset
uspto-grants-1980_06
Patent number
US04209626

Reaction notes

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