Dichloromethane → (4-Amino-5-methoxy-2-(trifluoromethyl)phenyl)(morpholino)methanone

Participants

Reaction Conditions

Reaction Steps

To (5-methoxy-4-nitro-2-(trifluoromethyl)phenyl)(morpholino)methanone (349 mg, 1.04 mmol) in ethanol (20 mL) and water (2 mL) was added SnCl2.2H2O (941 mg, 4.16 mmol). The mixture was heated to 65° C. for 2 h and then 2 M aqueous sodium hydroxide solution (20 mL) and DCM (20 mL) were added. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give (4-amino-5-methoxy-2-(trifluoromethyl)phenyl)(morpholino)methanone (250 mg, 79%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=305 at 2.87 min. 1H NMR (400 MHz, CDCl3): δ 6.94 (s, 1H), 6.64 (s, 1H), 4.07 (s, 2H), 3.92-3.67 (m, 4H), 3.89 (s, 3H), 3.62-3.52 (m, 2H), 3.25-3.19 (m, 2H).

Provenance & Evidence