反应详情

21.4 grams (0.114 mole) of 3-chloro-4-methylbenzoylchloride is added to a suspension of 15.2 g. (0.114 mole) aluminum chloride in 50 ml. 1,2-dichloroethane. The resulting solution is added dropwise to a chilled solution of 13.7 g. (0.114 mole) of 1-methylpyrrole-2-acetonitrile in 50 ml. 1,2-dichloroethane. After the addition is complete, the mixture is stirred for ten minutes at room temperature, and then heated to reflux for three minutes. It is poured into ice acidified with dilute HCl. The organic phase is separated and washed consecutively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution. It is then dried over anhydrous magnesium sulfate, and the solvent evaporated off. A white solid, 5-(3'-chloro-p-toluoyl)-1-methyl pyrrole-2-acetonitrile, precipitates from the resulting oily residue upon trituration with methanol which is purified by recrystallization from methanol, m.p. 116-118° C. Analysis: Calcd. for C15H13ClN2O: N, 10.26%. Found: N, 10.38%.

1. additionThe resulting solution is added dropwise to a chilled solution of 13.7 g
2. additionAfter the addition
3. temperatureheated
4. temperatureto reflux for three minutes
5. additionIt is poured into ice
6. customThe organic phase is separated
7. washwashed consecutively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution
8. dry with materialIt is then dried over anhydrous magnesium sulfate
9. customthe solvent evaporated off
10. customA white solid, 5-(3'-chloro-p-toluoyl)-1-methyl pyrrole-2-acetonitrile, precipitates from the resulting oily residue upon trituration with methanol which
11. customis purified by recrystallization from methanol, m.p. 116-118° C