Acetyl chloride → HCID 45086221, compound

Participants

Reaction Steps

3,5-Dimethyl-1H-pyrrole-2-carbonitrile (1.2 g, 10 mmol) was dissolved in anhydrous 1,2-dichloroethane (15 mL) and AlCl3 (2.93 g, 22 mmol) was added proportion-wise. The reaction vessel was purged with N2 and was cooled in an ice-water bath. AcCl (0.71 mL, 10 mmol) was added dropwise and the mixture was stirred for 1 h with cooling and for a further 3 h at room temperature. The reaction mixture was quenched by careful addition of 2 M aq HCl. The acidity of the mixture was adjusted to approximately pH 6 by addition of NaHCO3. After separation of the organic phase, the aqueous phase was extracted with EtOAc (3×100 mL). The combined organic phases were washed (H2O, then brine), dried (MgSO4), and filtered. The solvent was evaporated to afford of 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carbonitrile (1.42 g, 88%) as a pale tan solid. 1H-NMR (CDCl3) δ: 2.44 (s, 3H, CH3), 2.45 (s, 3H, CH3), 2.54 (s, 3H, CH3), 8.75 (br. s, 1H, NH).

Provenance & Evidence