반응 #1605768

반응 방정식

oxime

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

ammonia

→

amine

수율 45.0%

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

수율 45.0%

용매

MeOH

MeOH

반응 조건

후처리

1. 1
   기타was used in the next step without further purification
2. 2
   여과The slurry was filtered over celite and
3. 3
   농축concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   세척washed with water and brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

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.

출처