Cyclopropanecarboxylic acid 4-chloro-3-hydroxymethyl-benzylamide → Cyclopropanecarboxylic Acid 4-chloro-3-formyl-benzylamide

HRID 2428136Notes

Reaction equation

HRID 2428136 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[CH2:15][OH:16]>CC#N.O=[Mn]=O>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:11][CH2:12]2)=[O:9])=[CH:4][C:3]=1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 67148310Cyclopropanecarboxylic acid 4-chloro-3-hydroxymethyl-benzylamide

Product 1

HCID 86632362Cyclopropanecarboxylic Acid 4-chloro-3-formyl-benzylamideYield 94.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (6.29 g, 72.0 mmol) was added to a sol. of cyclopropanecarboxylic acid 4-chloro-3-hydroxymethyl-benzylamide (3.47 g, 14.0 mmol) in CH3CN (300 mL) at rt. The mixture was stirred for 3 h at rt, and MnO2 (2.52 g, 29.0 mmol) was added again. The mixture was stirred for 1 h at rt, and MnO2 (1.26 g, 14.0 mmol) was added again. The mixture was stirred for 1.5 h, and 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 (3.13 g, 91%) that was used further without purification. LC-MS: tR=0.80 min; ES+: 279.31.

Workup

  1. stirringThe mixture was stirred for 1 h at rt
  2. stirringThe mixture was stirred for 1.5 h
  3. filtrationwas filtered through celite
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-e40a95dcfb6343469488598a3c7562c6
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…