m-Toluidine → HCID 89650571, compound

Participants

Reaction Conditions

Reaction Steps

(Wallace, E., et. al., ibid.) m-toluidine (0.47 mL, 4.34 mmol) and conc. HCl (1 drop) were added to a solution of compound iii (1.00 g, 4.57 mmol) in ethanol (10 mL). The reaction mixture was heated at 80° C. for 3 h, cooled to room temperature and partitioned between water (15 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phase was dried (MgSO4) and reduced in vacuo to give the crude product as a brown oil. Column chromatography (SiO2), eluting with 12:1 Hexanes-EtOAc, gave compound iv. (0.670 g, 2.31 mmol, 51%) as a light orange oil, which solidified on standing, [M+H]+ m/z=291.0.

Provenance & Evidence