Methyl iodide → HCID 12837909, compound

HRID 2287988Notes

Reaction equation

HRID 2287988 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=[O:13])[NH:3]1.[H-].[Na+].[CH3:17]I>CN(C=O)C>[CH3:17][O:13][C:12](=[O:14])[CH2:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[NH:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 281699(3-Oxo-2,3-dihydro-1H-isoindol-1-yl)acetic acid

Product 1

HCID 12837909HCID 12837909, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2,3-dihydro-3-oxo-1H-isoindole-1-acetic acid (Rowe F. M., et al., J. Chem. Soc., 1098, 1936) (20 g, 104.6 mmol) in 100 mL of DMF is added to a suspension of NaH (2.5 g, 104.6 mmol) in 200 mL of DMF at room temperature under argon. Some cooling is required during the addition to keep the mixture at room temperature. The mixture is stirred at room temperature for 30 minutes. Methyl iodide (14.8 g, 104.6 mmol) is added, and the mixture is stirred at room temperature overnight. The reaction is quenched by addition of 5 mL of acetic acid, and the DMF is evaporated. Residual DMF is removed by heating the wet solid in a steam bath under high vacuum. The dried solid is stirred into 300 mL of CH2Cl2 for 1 hour. The solid is removed by filtration, and the filtrate is evaporated to give 12 g (56% yield) of 2,3-dihydro-3-oxo-1H-isoindole-1-acetic acid methyl ester.

Workup

  1. additionSome cooling is required during the addition
  2. customat room temperature
  3. stirringthe mixture is stirred at room temperature overnight
  4. customThe reaction is quenched by addition of 5 mL of acetic acid
  5. customthe DMF is evaporated
  6. customResidual DMF is removed
  7. temperatureby heating the wet solid in a steam bath under high vacuum
  8. stirringThe dried solid is stirred into 300 mL of CH2Cl2 for 1 hour
  9. customThe solid is removed by filtration
  10. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-03ad99dd8a224784ba430ae87c346453
Source dataset
uspto-grants-2000_07
Patent number
US06087364

Reaction notes

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