N-(4-Chloro-3-Hydroxymethyl-Phenyl)-3-Trifluoromethyl-Benzamide → N-(4-Chloro-3-Formyl-Phenyl)-3-Trifluoromethyl-Benzamide

HRID 1662810Notes

Reaction equation

HRID 1662810 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[CH2:21][OH:22]>C1(C)C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[CH:21]=[O:22]

Participants

4

Reactant 1

HCID 58901699N-(4-Chloro-3-Hydroxymethyl-Phenyl)-3-Trifluoromethyl-Benzamide

Product 1

HCID 59652741N-(4-Chloro-3-Formyl-Phenyl)-3-Trifluoromethyl-BenzamideYield 43.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

The solution of intermediate 7 (Example 13) (700 mg, 2.1 mmol) and MnO2 (1.8 g, 21 mmol) in anhydrous toluene (30 mL) was refluxed for 2 h. After cooling down, the MnO2 was removed by filtration. The solvent was removed by reduced pressure. The solid was re-crystallized from chloroform to yield an off-white solid (300 mg, 43%).

Workup

  1. temperatureAfter cooling down
  2. customthe MnO2 was removed by filtration
  3. customThe solvent was removed by reduced pressure
  4. customThe solid was re-crystallized from chloroform

Sources & evidence

ORD record
ord-a89846a9e8e24fb6a584fab301b44b40
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

Loading…