[O:1]=[CH:2][C:3](Cl)(Cl)Cl.Cl.[NH2:8][OH:9].[NH2:10][C:11]1[C:12](O)=[CH:13][C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[CH:20]=1.Cl.C([O-])(=O)C.[Na+]>O>[O:1]1[C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[N:10]=[C:2]1[CH:3]=[N:8][OH:9])[CH2:18][CH2:17][CH2:16][CH2:15]3Chloral (10.7 g in 20 ml of water) and hydroxylamine hydrochloride (4.5 g in 10 ml of water) was added simultaneously to a solution of 5,6,7,8-tetrahydro-3-amino-2-naphthol (7 g) in 50 ml of water containing 3.8 ml of concentrated HCl at 60°-70° C. The reaction mixture was neutralized with sodium acetate (25 g) to keep the PH 4.5 over a period of 1 hour. The reaction mixture was cooled, filtered, and dried thoroughly to give 8.5 g of 5,6,7,8-tetrahydronaphth[2,3-d]oxazole-2-aldoxime as dark solid product.
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