p-Fluoronitrobenzene → HCID 7062386, compound

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[O:17][C@@H:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][C@H:16]1[O:17][C@@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1

Participants

Procedure

1-Fluoro-4-nitrobenzene (4.9 g, 34.75 mmol) was added to a stirred mixture of cis-2,6-dimethylmorpholine (44.4 g, 38.26 mmol) and anhydrous potassium carbonate (2.5 g, 18.12 mmol) in acetonitrile (50 mL). The mixture was heated under reflux for 19 h, cooled, filtered and the solid washed with acetonitrile. The filtrate was concentrated by evaporation to give the title compound (8.1 g, 99%) as a solid; 1H NMR δ (CDCl3): 8.13 (2H, d), 6.82 (2H, d), 3.76 (2H, m), 3.66 (2H, dt), 2.61 (2H, t), 1.28 (6H, d); MS m/e MH+: 237.