Tin tetrachloride → 5-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 1039090노트

반응식

HRID 1039090 반응식
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:11]([O-])=O)[CH:8]=2)[C:3]1=[O:14].[Sn](Cl)(Cl)(Cl)Cl>CCO.O>[NH2:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[O:14])[N:2]([CH3:1])[CH2:10]2

참가 물질

5

반응물 2

HCID 24287Tin tetrachlorideHCID 592252992-Methyl-5-nitroisoindolin-1-one

생성물 1

HCID 529112475-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
79 °C

실험 절차

The 2-methyl-5-nitroisoindolin-1-one (50 mg, 0.26 mmol) was dissolved in EtOH (1.3 ml) with heating, and tin chloride (117 mg, 0.52 mmol) added. The solution was stirred at 79° C. for 2 hours. The mixture was cooled to RT, diluted with 4:1 water:saturated sodium bicarbonate (aq, 100 ml), extracted with EtOAc (3×100 ml), the organics combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 5% MeOH:DCM+1% TEA to give the titled compound.

후처리

  1. temperaturewith heating
  2. temperatureThe mixture was cooled to RT
  3. extractionsaturated sodium bicarbonate (aq, 100 ml), extracted with EtOAc (3×100 ml)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe volatiles removed in vacuum
  8. customThe product was purified by chromatography on SiO2 eluting with 5% MeOH

출처 및 근거

ORD 기록
ord-86ee7ff97e5e4cdf86363b1665f13cd9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552022B2

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