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

HRID 1039090ノート

反応式

HRID 1039090 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
79 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-86ee7ff97e5e4cdf86363b1665f13cd9
出典データセット
uspto-grants-2013_10
特許番号
US08552022B2

反応ノート

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