4-Nitroaniline → 2-Methyl-6-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

4-Nitroaniline (6 g, 38 mmol) was dissolved in HCl (6N, 200 mL), the mixture was heated at 100° C. A solution of (E)-but-2-enal (7.2 mL, 76 mmol) in toluene (60 mL) was added dropwise, and the reaction was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and basified with aqueous KOH until pH=12. The mixture was extracted with EtOAc and the organic layer was washed with brine and dried over anhydrous Na2SO4. 2-Methyl-6-nitroquinoline was obtained after purification by column chromatography (hexane: EtOAc=20:1) (5.8 g, 81.2%). MS [M++1]=189, LC-MS: tR=1.64 min.

Provenance & Evidence