HCID 20339624, compound → HCID 20339572, compound

HRID 1395541Notes

Reaction equation

HRID 1395541 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8](Cl)[N:7]=1.[H][H]>[OH-].[K+].CO>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 20339624HCID 20339624, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20339572HCID 20339572, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 2-(2-dimethylaminoethylamino)-4-trifluoromethyl-6-chloropyridine (5.8 g., 0.022 mole) (from Example 53 Part A) in 2.5% potassium hydroxide in methanol (75 ml.) containing 5% palladium-on-calcium carbonate (0.5 g.) in hydrogenated in a Parr apparatus at 50 psi of hydrogen until 0.022 mole of hydrogen is taken up (24 hours). The catalyst is filtered and the solvent removed under vacuum. The residue is dissolved in water and the product is extracted into methylene chloride, dried over anhydrous sodium sulfate and evaporated to give the oily product (5.0 g.) which is used without further purification in the succeeding step.

Workup

  1. custom(24 hours)
  2. filtrationThe catalyst is filtered
  3. customthe solvent removed under vacuum
  4. dissolutionThe residue is dissolved in water
  5. extractionthe product is extracted into methylene chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customto give the oily product (5.0 g.) which
  9. customis used without further purification in the succeeding step

Sources & evidence

ORD record
ord-92ccd62084a64746ae3c05db6253a341
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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