[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([NH2:16])[CH:7]=1)=[O:5])[CH3:2].[N:17]([O-])=O.[Na+].O.O.[Cl:23][Sn]Cl>Cl>[ClH:23].[NH:16]([C:8]1[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH2:17]To a solution of 3-aminonaphthalene-1-carboxylic acid ethyl ester (2 g, 9.3 mmol) in conc. HCl (2 mL) was added dropwise an aqueous solution of NaNO2 (0.63 g, 9.3 mmol) at 0° C. The resulted mixture was stirred for 1 h and then treated dropwise with a solution of SnCl2.2H2O (4.2 g, 18.6 mmol) in conc. HCl (10 mL) at 0° C. The reaction mixture was stirred for 2 h at RT. precipitate was collected and washed with EtOH and Et2O to yield ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride as a white solid (1.5 g), which was used for the next reaction without further purification.
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