Trifluoroacetic acid → HCID 3773118, compound

HRID 1955789Notes

Reaction equation

HRID 1955789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:16]#[N:17])[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(O)(C(F)(F)F)=O.[H][H]>[Pd].CO>[NH2:17][CH2:16][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 19073225Methyl cyano(3,4-dimethoxyphenyl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 3773118HCID 3773118, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A MeOH solution (100 mL) containing methyl 3,4-dimethoxyphenylcyanoacetate (1.2 g, 5.1 mmol), TFA (1 mL), and 50 mg of 10% Pd/C was shaken on a Parr shaker for 20 hours under 30 psi of hydrogen. The reaction was filtered, concentrated, dissolved in H2O, and extracted 2× with Et2O. The pH was adjusted to ~10 and the mixture extracted 3× with EtOAc. The EtOAc fractions were dried over Na2SO4 and concentrated to yield 400 mg (32%) of the title compound.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. dissolutiondissolved in H2O
  4. extractionextracted 2× with Et2O
  5. extractionthe mixture extracted 3× with EtOAc
  6. dry with materialThe EtOAc fractions were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f70a40aeaed443b68081e7b32c6f617e
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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