Hydrochloric Acid → HCID 67132219, compound

Participants

Reaction Steps

To a stirred solution of 2-methylbenzyl cyamide (3.11 ml) in CCl4 (100 ml) was added N-bromosuccinimide (4.89 g) and a catalytic amount of benzoyl peroxide. The mixtures was heated to reflux and stirred for 1.5 hours. The mixture was cooled to room temperature and was filtrated. The filtrate was evaporated under reduced pressure and the residue was dissolved in a minimum amount of EtOAc and petroleum ether was added. The resulting solid material was isolated by filtration and washed with petroleum ether and gave (2-bromomethyl-phenyl)-acetonitrile (926 mg). The filtrate was evaporated under reduced pressure and the residue was subjected to chromatography on silica gel (elution petroleum ether/EtOAc 10/1, v/v) affording an additional amount of (2-bromomethyl-phenyl)-acetonitrile (1.45 g). This benzyl bromide (2.27 g) was dissolved in NMP and N-hydroxyphthalimide (1.53 g) was added followed by drop-wise addition of 1,8-diazabicyclo[5,4,0]-undec-7-ene (1.40 ml). The reaction mixture was stirred at room temperature for 5 hours. 1M HCl aq. (173 ml) was added and the resulting precipitated material was isolated by filtration and washed with water and dried under high vacuum and gave [2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-phenyl]-acetonitrile (2.25 g). This phthalimide intermediate (2.23 g) was dissolved in dichloromethane and methyl-hydrazine (1.1 eq.) was added. The reaction mixture was stirred at room temperature for 30 minutes and the formed solid material was removed by filtration. The filtrate was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel (petroleum ether/EtOAc 3/1, v/v) and gave the title compound. 13C-NMR (CDCl3) δ 135.0, 130.9, 129.7, 129.2, 129.2, 128.3, 118.0, 75.8, 21.1.

Provenance & Evidence