O[CH:2]1[C:11](=C)[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[C:3]1=O.[NH:16]([CH2:18][CH:19]([OH:21])[CH3:20])[NH2:17].O.[C:23]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH2:11][C:2]3[CH:23]=[N:17][N:16]([CH2:18][CH:19]([OH:21])[CH3:20])[C:3]=3[C:4]=2[CH:5]=1A solution of 1.63 g (7.98 mmol) of 2-hydroxy-methylene-7-methoxy-1-tetralone, 0.87 g (9.65 mmol) of (RS)-1-hydrazino-2-propanol and 100 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator for 1.5 hours. After concentration in a vacuum, the reaction mixture S was purified by column chromatography on silica gel (ethyl acetate/hexane 1:1). 1.52 g (74%) of (RS)-1-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-propan-2-ol were obtained as a yellow oil which was used directly in the next reaction.
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