2-tert-Butylaniline → HCID 67208015, compound
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[C:22]([C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH2:28])([CH3:25])([CH3:24])[CH3:23]>CC#N>[C:22]([C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH:28][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20])([CH3:25])([CH3:23])[CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-3-nitroquinoline (for a preparation see Intermediate 16) (2.2 g, 7.2 mmol) and 2-tert-butylaniline (1.2 g, 8 mmol) in CH3CN (20 ml) was refluxed for 1 h. The solvent was evaporated in vacuo and the residue treated with an aqueous solution of sodium hydroxide N, extracted with DCM, washed with water and dried over Na2SO4. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (99:1) to give the title compound as a yellow solid (2.4 g, 80%). [APCI-MS] m/z: 417 MH+, Rt 3.73 min. NMR (300 MHz, DMSO-d6, ppm) δ: 9.87 (brs, 1H), 8.92 (s, 1H), 8.34 (d, J=8.7 Hz, 1H), 7.82 (s, 1H), 7.50 (d, J=8.9 Hz, 1H), 7.25-6.91 (m, 4H), 2.32 (s, 3H), 2.15 (s, 3H).