[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N+:19]([O-])=O)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.CCOC(C)=O.CC(O)=O.[H][H]>CO.[Pt]>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([NH2:19])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1
A solution of 2-chloro-4-(4-nitronaphthalen-1-ylthio)pyridine (1.68 g, 5.30 mmol) in a mixture of MeOH (30 mL), EtOAc (100 mL) and AcOH (10 mL) was subjected to hydrogenation by two passages through a Thales H-cube (1.0 mL min−1, 50° C., 70 mm, 10% Pt—C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo to afford 4-(2-chloropyridin-4-ylthio) naphthalen-1-amine as a brown oil (1.40 g, 90% purity (LCMS), 83%); Rt 4.50 min (Method 1 basic); m/z 287 (M+H)+ (ES+). The material so obtained was used in the next step without further purification.
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