反応 #1605768

反応方程式

oxime

5-methoxy-2,3-dihydroinden-1-one oxime

ammonia

→

amine

収率 45.0%

5-methoxy-2,3-dihydro-1H-inden-1-amine

収率 45.0%

溶媒

MeOH

MeOH

反応条件

後処理

1. 1
   その他was used in the next step without further purification
2. 2
   ろ過The slurry was filtered over celite and
3. 3
   濃縮concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   洗浄washed with water and brine
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo

実験手順

5-Methoxy-2,3-dihydromden-1-one (Ig, 6.17 mmol) was added to a solution of hydroxylamine HCl (730 mg, 10.5 mmol) in 10 ml of water. The mixture was brought up to 70° C. and a solution of sodium acetate (1.4 g, 16.7 mmol) in 7 mL of H2O, 14 ml of MeOH, 3 ml of THF was added. After stirring for 1.5 h at 70° C., 10 ml of H2O was added to produce a precipitate and the suspension was allowed to stir for 2 h. The precipitate was collected by filtration to give 5-methoxy-2,3-dihydroinden-1-one oxime almost quantitatively and was used in the next step without further purification. The oxime (0.5 g, 2.82 mmol) was dissolved in MeOH and a catalytic amount of Raney nickel and 25 mL of ammonia solution in MeOH (7N) was added. The reaction was stirred at r.t. overnight under H2. The slurry was filtered over celite and concentrated in vacuo, diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to give the crude title amine (yield, 45%). The crude amine was used without further purification.

出典