m-Chloroperbenzoic acid → HCID 85040066, compound
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:22]=[C:21]([C:23]#[C:24][CH2:25][N:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>ClCCl>[Cl:12][C:13]1[CH:22]=[C:21]([C:23](=[O:6])[CH:24]=[CH:25][N:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Gradually, 3-chloroperoxybenzoic acid (10.76 g) was added to a solution of 2-chloro-4-(3-dimethylamino-propyn-1yl)-benzoic acid, methyl -ester (15.07 g in dichloromethane (40 ml), at a rate to maintain the reaction temperature at −20° C. The mixture was stirred for 10-15 minutes. The resulting N-oxide was purified by chromatography on Activity Grade I basic alumina (215 g), eluting with 10% methanol/dichloromethane. The solvent was evaporated in vacuo between 12 to 18° C. The resulting residue was dissolved in methanol (100 ml) and heated at 60-65° C. with stirring for 18 hours. After removing the solvent in vacuo, and the product was purified by column chromatography on silica gel (190 g), eluting with 70% ethyl acetate/hexane. Trituration with diethyl ether containing some hexane afforded the title compound as a solid (5.68 g), m.p. 92-96° C.