Nitric Acid → HCID 178486766, compound
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([C:15]([OH:21])=[CH:16][CH:17]=[N:18]3)=[CH:13][CH:12]=2)=[C:9]([CH3:22])[O:8][N:7]=1.[C:23](O)(=[O:26])CC>>[CH3:5][C:6]1[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([C:15]([OH:21])=[C:16]([N+:1]([O-:4])=[O:2])[CH:17]=[N:18]3)=[CH:13][C:12]=2[O:26][CH3:23])=[C:9]([CH3:22])[O:8][N:7]=1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
Nitric acid (10 ml) was added slowly to a solution of 7-(3,5-dimethyl-4-isoxazolyl)-4-quinolinol (for a preparation see Intermediate 14 (28 g, 104 mmol) in propanoic acid (450 ml) at room temperature, followed by heating the reaction mixture to 100° C. for 1 h. After cooling with an ice bath, the precipitate was filtered off, washed with pentane to give the title compound as a yellow powder (27 g, 82%). [APCI-MS] m/z: 314 [M−H]−, Rt 2.12 min. 1H NMR (300 MHz, DMSO-d6, ppm) δ: 13.06 (s, 1H), 9.26 (s, 1H), 7.84 (s, 1H), 7.67 (s, 1H), 3.98 (s, 3H), 2.39 (s, 3H), 2.19 (s, 3H).