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

HRID 722956Notes

Reaction equation

HRID 722956 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. customthe solvent was evaporated under reduced pressure
  2. filtrationThe resulting residue was filtered
  3. washwashed with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ebe25e175a6343d78439f08294ade04f
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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