Sodium Hydroxide → 7-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 2382638Notes

Reaction equation

HRID 2382638 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[C:5]([N+:11]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:14].O.O.Cl[Sn]Cl.[OH-].[Na+]>CCOC(C)=O>[NH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3](=[O:14])[N:2]([CH3:1])[CH2:10]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 587485312-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 450887127-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 96.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, a solution of N-Methyl-7-nitro-2,3-dihydroisoindole-1-one (561.0 mg, 2.92 mmol) in EtOAc (8.4 mL) is treated with SnCl2.2H2O (2.68 g), stirred at 80° C. under reflux for 5 h, and treated with 30 mL of 5N NaOH at 0° C. After the both layers are separated, the aqueous layer is extracted with EtOAc (2×8 mL), the combined extracts are washed with brine (5 mL), dried (MgSO4), and evaporated to give 7-Amino-N-methyl-2,3-dihydroisoindole-1-one (455.9 g, 2.81 mmol) in 96%. Yellow solid. Rf (CH2Cl2/EtOAC 1:1) 0.53. 1H-NMR (400 MHz, CDCl3) 3.12 (s), 4.28 (s), 5.20 (br. s), 6.56 (d, J=8.0), 6.68 (d, J=8.0), 7.21 (dd, J=8.0, 8.0).

Workup

  1. temperatureunder reflux for 5 h
  2. customAfter the both layers are separated
  3. extractionthe aqueous layer is extracted with EtOAc (2×8 mL)
  4. washthe combined extracts are washed with brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-55b4b0961fe440d4b654f9853295f3fa
Source dataset
uspto-grants-2012_09
Patent number
US08263590B2

Reaction notes

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