[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([C:21]#[N:22])=[CH:13][C:12]=1[N+:23]([O-])=O)[C:6](=[O:10])[O:7][CH2:8][CH3:9].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:23][C:12]1[CH:13]=[C:14]([C:21]#[N:22])[CH:15]=[C:16]([C:17]([F:19])([F:20])[F:18])[C:11]=1[N:5]([CH2:4][C:3]1[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=1[Cl:1])[C:6](=[O:10])[O:7][CH2:8][CH3:9]Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate (298.4 mg) was dissolved in methanol (30 ml), and to the solution were added titanium(III) chloride solution (6.672 g) under ice-cooling. After stirring for 20 minutes, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (315.4 mg, quantitative yield).
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