O-Toluidine → HCID 18630160, compound

Participants

Reaction Steps

The compound of Example c (0.0035 mol, 0.95 g), 15 mL thionyl chloride, and 1 drop of DMF were combined and stirred at RT overnight. Toluene (50 mL) was added and the mixture concentrated to dryness. This process was repeated three times, and the residue dissolved in CH2Cl2 (50 mL). 2-Methylaniline (0.0035 mol, 0.37 g) and triethylamine (0.0035 mol, 0.39 g) were added and the mixture was stirred at RT overnight. The mixture was washed with 10% HCl and twice with water; dried (MgSO4) and concentrated. The title compound was recrystallized from hexanes as a tan solid in 71% yield. m.p. 113-115° C.

Provenance & Evidence