Potassium Carbonate → 2-(2-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione

HRID 1410040Notes

Reaction equation

HRID 1410040 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH:5]=[CH:4][NH:3]1.[C:21]([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH3:21][N:3]1[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:7][C:2]1=[O:1]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 683792552-(2-(2-Oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 683791842-(2-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dioneYield 74.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione (300 mg, 1.1 mmol) CH3I (1.0 g, 7 mmol) and K2CO3 (700 mg, 5 mmol) in 30 mL of DCM and 10 mL of DMF was stirred at room temperature for 3 days. 30 mL of DCM was added. The mixture was washed with H2O (3×30 mL), dried over anhydrous sodium sulfate, concentrated under reduce pressure to give 2-(2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione (230 mg, 73%) as a white solid. LC-MS: 283 [M+H]+, tR=1.29 min.

Workup

  1. washThe mixture was washed with H2O (3×30 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-73837cbc04e04260ad4c2ff0ae0b9064
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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