[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([OH:9])[CH:3]=1.[N:10]([O-])=O.[Na+].[Sn](Cl)[Cl:15]>O.Cl>[ClH:15].[NH:1]([C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([OH:9])[CH:3]=1)[NH2:10]To an ice cold slurry of 4-amino-2-hydroxytoluene (6.22 g, 50.0 mmol), ice (10.0 g) and hydrochloric acid (37% aqueous, 15.0 mL) was added an ice-cold solution of sodium nitrite (3.49 g, 50.0 mmol) in water (10.0 mL) over 30 min. The resultant slurry was added over 30 min to an ice-cold slurry of tin (II) chloride (25.3 g, 133 mmol) in water (30.0 mL) and hydrochloric acid (37% aqueous, 30.0 mL) and the reaction stirred overnight. The mixture was cooled in an ice/water bath and the solid collected by filtration, washing with ice-cold cyclohexane. The residue was dried in vacuo at 50° C. to give the title compound (water retained, 11.1 g). 1H NMR (300 MHz, d4-MeOD): 2.12 (3H, s), 6.38 (1H, dd, J=2.3, 8.0 Hz), 6.44 (1H, d, J=2.3 Hz), 7.02 (1H, d, J=8.1 Hz).
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