HCID 67208015, compound → 7-(3,5-dimethyl-4-isoxazolyl)-N4-(phenylmethyl)-3,4-quinolinediamine
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=C[C:6]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[C:23]([CH3:28])=[N:24][O:25][C:26]=3[CH3:27])=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[N+:29]([O-])=O)(C)(C)[CH3:2]>C(O)C.C1COCC1>[CH3:28][C:23]1[C:22]([C:18]2[CH:17]=[C:16]3[C:21]([C:12]([NH:11][CH2:6][C:5]4[CH:1]=[CH:2][CH:8]=[CH:9][CH:10]=4)=[C:13]([NH2:29])[CH:14]=[N:15]3)=[CH:20][CH:19]=2)=[C:26]([CH3:27])[O:25][N:24]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-[2-(tert-butyl)phenyl]-7-(3,5-dimethyl-4-isoxazolyl)-3-nitro-4-quinolinamine (see Intermediate 19, 2.4 g, 5.77 mmol) in a mixture of ethanol (60 ml) and THF (20 ml), was added SnCl2,2H2O (7.81 g, 34.6 mmol). The reaction mixture was refluxed for 3 h and then concentrated to dryness. The resulting residue was poured into aqueous sodium hydroxide. The organic phase was extracted with EtOAc, washed with water, dried and concentrated to give the title compound as a yellow solid (2 g, 71%). [APCI-MS] m/z: 387 MH+, Rt 3.37 min.