N-(4-Chloro-3-hydroxymethyl-benzyl)-propionamide → N-(4-chloro-3-formylbenzyl)propionamide

HRID 2428132Notes

Reaction equation

HRID 2428132 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][C:3]=1[CH2:14][OH:15]>CC#N.O=[Mn]=O>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][C:3]=1[CH:14]=[O:15]

Participants

4

Reactant 1

HCID 67148202N-(4-Chloro-3-hydroxymethyl-benzyl)-propionamide

Product 1

HCID 86632361N-(4-chloro-3-formylbenzyl)propionamideYield 93%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (5.61 g, 65.7 mmol) was added to a sol. of N-(4-chloro-3-hydroxymethyl-benzyl)-propionamide (2.99 g, 13.1 mmol) in CH3CN (255 mL) at rt. The mixture was stirred for 3 h at rt, and MnO2 (2.24 g, 26.2 mmol) was added again. The mixture was stirred for 1 h at rt, and the mixture was filtered through celite. The filtrate was evaporated under reduced pressure, and the residue was dried under high vacuum to yield the crude title compound (2.74 g, 93%) that was used further without purification. LC-MS: tR=0.76 min; ES+: 267.27.

Workup

  1. stirringThe mixture was stirred for 1 h at rt
  2. filtrationthe mixture was filtered through celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-a0eaa42206434cfcbb4ec045294a6af7
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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