N-Phthaloylglycine → 2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-

HRID 747596Notes

Reaction equation

HRID 747596 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][C:13]([OH:15])=O.C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C=O)C>[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][C:13]([Cl:19])=[O:15]

Participants

5

Reactant 2

HCID 20825N-PhthaloylglycineHCID 65578Oxalyl chloride

Product 1

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 10.25 g of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid dissolved in 50 ml of dichloromethane are added, at room temperature, 4.6 ml of oxalyl chloride and 2 drops of DMF, and the mixture is left for 18 hours at room temperature. The resulting mixture is evaporated to dryness to give 11 g of the expected product.

Workup

  1. additionare added, at room temperature
  2. customThe resulting mixture is evaporated to dryness

Sources & evidence

ORD record
ord-981b4b2ddff44aa7a8248995a0bc64d0
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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