Hydrochloric Acid → 5-Amino-1-(4-chloro-benzyl)-1,2-dihydro-indazol-3-one

反応式

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=3)[C:9](=[O:19])[NH:8]2)=[CH:4][CH:3]=1.Cl.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>>[NH2:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:5]1[CH:20]=[CH:21][C:2]([Cl:1])=[CH:3][CH:4]=1)[NH:8][C:9]2=[O:19]

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 24479Stannous Chloride

HCID 516892Sodium Bicarbonate

HCID 68833180HCID 68833180、化合物

生成物 1

HCID 105642105-Amino-1-(4-chloro-benzyl)-1,2-dihydro-indazol-3-one収率 76.4%

反応条件

温度: 85 °C

実験手順

To 1-(4-chloro-benzyl)-5-nitro-1,2-dihydro-indazol-3-one (0.45 g) was added HCl (37% aq.) solution (5 mL) followed by SnCl2.dihydrate (1.9 g). The mixture was heated to 85° C. for one hour. The reaction was then neutralized with sodium bicarbonate solution, filtered, and the filtrate extracted with EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and reduced in vacuo. Flash column chromatography of the residue over silica gel eluting with methylene chloride/methanol afforded the desired 5-amino-1-(4-chloro-benzyl)-1,2-dihydro-indazol-3-one (0.31 g) as a dark brown solid. MS (ESI+): 274.4 [M+H]+).