[O:1]=[CH:2][C:3](Cl)(Cl)Cl.[NH2:7][OH:8].[NH2:9][C:10]1[C:11](O)=[CH:12][C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH:19]=1.Cl.C([O-])(=O)C.[Na+]>O>[O:1]1[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:10]=2[N:9]=[C:2]1[CH:3]=[N:7][OH:8])[CH2:17][CH2:16][CH2:15][CH2:14]3Chloral (10.7 g in 20 ml of water) and hydroxylamine hydrchloride (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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