Tetrahydrofuran → 4 - nitro - 2(3H) - benzoxazolone
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C1C[O:15][CH2:14]C1>CCOC(C)=O>[N+:8]([C:7]1[C:2]2[NH:1][C:14](=[O:15])[O:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2-amino-3-nitrophenol 3b (2 g, 13.00 mmol) dissolved in THF (50 ml) was added in one portion DCI (1.5 equiv., 19.6 mmol, 3.176 g) and the reaction was refluxed for 4 hours. (TLC AcOEt 1/petroleum ether 1). The reaction was evaporated and the crude material was dissolved in HCL 2N and extracted 3 times with chloroform. The combined organic phases were washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The crude solid was crystallized from ether giving 1.5 g of a beige solid. Yield=65% 1HNMR (DMSO, 200 MHz) δ 7.27 (1H, t, J=7.8 Hz), 7.72 (1H, dd, J=8.2 Hz, J′=1 Hz), 7.93 (1H, dd, J=8.4 Hz, J′=0.6 Hz), 12.64 (1H, bs)