N-(4-Chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamide → N-(4-Chloro-3-formyl-benzyl)-3,3,3-trifluoro-propionamide

HRID 1715402Notes

Reaction equation

HRID 1715402 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[CH2:17][OH:18]>CC#N.O=[Mn]=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[CH:17]=[O:18]

Participants

4

Reactant 1

HCID 67148258N-(4-Chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamide

Product 1

HCID 86622955N-(4-Chloro-3-formyl-benzyl)-3,3,3-trifluoro-propionamideYield 100.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (1.44 g, 14.9 mmol) was added to a sol. of N-(4-chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamide (841 mg, 2.99 mmol) in CH3CN (60 mL). The mixture was stirred at rt for 3 h. MnO2 (1.44 g, 14.9 mmol) was added again, and the mixture was stirred for 90 min. The mixture was filtered over Celite, and the precipitate was washed with CH3CN and CH2Cl2. The solvents were removed under reduced pressure, and the residue was dried under high vacuum, yielding the crude title compound (840 mg, quantitative yield) that was used without purification. LC-MS: tR=0.84 min; ES+: 341.21.

Workup

  1. stirringthe mixture was stirred for 90 min
  2. filtrationThe mixture was filtered over Celite
  3. washthe precipitate was washed with CH3CN and CH2Cl2
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-1a6706d383944ace904765e64c725408
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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