[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]([CH3:11])[CH3:10])[C:3]=1[CH2:12][OH:13]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:12][OH:13].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]([CH3:11])[CH3:10])[C:3]=1[CH:12]=[O:13]A mixture of [2-chloro-6-(isopropylamino)phenyl]methanol, 5-chloro-2,2-dimethyl-1,4-dihydro-2H-3,1-benzoxazine (2.7 g, ratio; 1:1, step 2) and manganese dioxide (3.9 g, 33.8 mmol) in toluene (50 mL) was stirred at reflux temperature for 16 h. The mixture was filtrated through a pad of Celite and the filtrate was concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:30) to give 1.2 g (45% from (2-amino-6-chlorophenyl)methanol) of the title compound as a yellow solid.
Wird geladen…
