Dimethylformamide → 2-Methyl-1,3-dioxo-5-isoindolinecarbonyl chloride

HRID 2374612Notes

Reaction equation

HRID 2374612 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11]C=[C:13](C(O)=O)[CH:14]=2)[C:9]1=[O:21].CN(C)C=O>O1CCCC1>[CH3:7][N:8]1[C:9](=[O:21])[C:10]2[C:15](=[CH:14][CH:13]=[C:1]([C:2]([Cl:4])=[O:3])[CH:11]=2)[C:16]1=[O:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8834312-Methyl-1,3-dioxoisoindoline-5-carboxylic acid

Product 1

HCID 145310592-Methyl-1,3-dioxo-5-isoindolinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (5.86 ml) was added by portions to a solution of 2-methyl-1,3-dioxo-5-isoindolinecarboxylic acid (9.2 g) obtained in Reference Example 229. and dimethylformamide (catalytic amount) in tetrahydrofuran (100 ml) at room temperature. After stirred at room temperature for 1 hour, the solvent was evaporated under reduced pressure. The resulting residue was filtered, washed with diethyl ether and dried under reduced pressure to give the title compound as a white solid.

Workup

  1. customobtained in Reference Example 229
  2. customat room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. filtrationThe resulting residue was filtered
  5. washwashed with diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ca8dd9aac5a4b84999546d35c26eaa9
Source dataset
uspto-grants-2008_12
Patent number
US07462628B2

Reaction notes

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