Hydrochloric Acid → 5,6-Dimethoxy-1H-indazol-3-amine

반응식

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.[N:15]([O-])=O.[Na+]>>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:12][CH3:13])=[C:5]([O:10][CH3:11])[CH:6]=2)[NH:1][N:15]=1

참가 물질

반응물 3

HCID 313Hydrochloric Acid2회

HCID 7359672-Amino-4,5-dimethoxybenzonitrile

HCID 23668193Sodium Nitrite

생성물 1

HCID 214091945,6-Dimethoxy-1H-indazol-3-amine수율 147.5%

실험 절차

To a solution of 6-aminoveratronitrile (39 g, 0.2 mole) and conc. hydrochloric acid (329 ml) was added a solution of sodium nitrite (17 g, 0.25 mole in minimum amt. of water). The temperature was held below 0° during the addition. Keeping the temperature between 0° to 20° the resulting solution was added dropwise to stannous chloride (33.3 g, 1.76 mole) and conc. hydrochloric acid (153 ml). The precipitate was filtered and air dried overnight. The filter cake was placed in water (1100 ml), refluxed for 20-30 min and then filtered. The filtrate was cooled and then treated with sodium hydroxide (10% - 290 ml) to precipitate a tan solid. This solid was air dried at 60° to yield 57 g of 3-amino-5,6-dimethoxyindazole.