Hydroxyacetone → 1-Propanol, 2-[(2,3,4-trifluorophenyl)amino]-

HRID 1603319Notes

Reaction equation

HRID 1603319 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[OH:11][CH2:12][C:13](=O)[CH3:14]>[Pd].CO>[OH:11][CH2:12][CH:13]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([F:10])=[C:8]([F:9])[C:2]=1[F:1])[CH3:14]

Participants

5

Reactant 2

HCID 8299Hydroxyacetone3×HCID 774682,3,4-Trifluoroaniline3×

Product 1

HCID 98590971-Propanol, 2-[(2,3,4-trifluorophenyl)amino]-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

2,3,4-Trifluoroaniline was reductively alkylated in the presence of hydroxyacetone using a palladium on carbon catalyst. 30 g of a 5% Pd/C catalyst (57.3% H2 0)) was slurried in 200 ml of absolute methanol. The mixture was allowed to settle and 90-95% of the liquid was decanted. The process was then repeated three times. 2,3,4-trifluoroaniline (118 g, 0.8 mole) of was charged into a glass autoclave liner containing the catalyst. Hydroxyacetone (80 g, 1.08 mole) was then added and the mixture was purged with nitrogen. Hydrogenation was initiated at 65° C. and continued to a maximum temperature of 107° C. Hydrogen uptake continued for one hour at a pressure of between 430 and 450 psi at which time 75% of the alkylated product (3) was obtained with the remainder being unreacted 2,3,4-trifluoroaniline and hydroxyacetone.

Workup

  1. custom90-95% of the liquid was decanted
  2. additioncontaining the catalyst
  3. customthe mixture was purged with nitrogen
  4. customwas initiated at 65° C.
  5. customcontinued to a maximum temperature of 107° C
  6. customwas obtained with the remainder

Sources & evidence

ORD record
ord-fb081366fab44b8394d4c9d1b97ac8cf
Source dataset
uspto-grants-1999_11
Patent number
US05986140

Reaction notes

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