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

HRID 1039090Notes

Reaction equation

HRID 1039090 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
79 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-86ee7ff97e5e4cdf86363b1665f13cd9
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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