Dimethylformamide → 1,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chloride

HRID 520305Notes

Reaction equation

HRID 520305 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]([OH:16])=O.C(Cl)(=O)C([Cl:20])=O.CN(C=O)C>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]([Cl:20])=[O:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 768593-Phthalimidopropionic acid

Product 1

HCID 869661,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chlorideYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 137g (20.0 g, 91 mmol) in DCM (250 mL) were added oxalyl chloride (13.8 g, 109 mmol) and DMF (0.1 mL). See FIG. 2. The mixture was stirred at RT for 4 h. Upon reaction completion, the mixture was concentrated to give 3-(1,3-dioxoisoindolin-2-yl)propanoyl chloride 137h (20.0 g, 92%) as a white solid.

Workup

  1. customUpon reaction completion
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-b6900d05179d4d31bae4a8dc6a913546
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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