Sulfuric Acid → (1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester

HRID 1866314Notes

Reaction equation

HRID 1866314 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:14].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)CCC>[CH2:4]([O:14][C:13](=[O:15])[CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 20825N-PhthaloylglycineHCID 516892Sodium Bicarbonate

Product 1

HCID 357739(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl esterYield 194.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 160 ml of butanol, 20.0 g of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid (94.6 mmol) and 2.0 ml of concentrated sulfuric acid was refluxed with stirring for 24 h. Then 5 g of sodium bicarbonate were added in portions, stirring continued at r.t. for 5 min and the solvent evaporated in vacuo. The residue was partitioned between 100 ml of water and 100 ml of ethyl acetate. The organic phase was washed with 100 ml of brine, dried over sodium sulfate and was evaporated in vacuo to give a yellowish oil that later solidified. 24.02 g of the title compound were obtained; MS-(+)-ion: M+1=261.9.

Workup

  1. temperaturewas refluxed
  2. stirringstirring
  3. waitcontinued at r.t. for 5 min
  4. customthe solvent evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of water and 100 ml of ethyl acetate
  6. washThe organic phase was washed with 100 ml of brine
  7. dry with materialdried over sodium sulfate
  8. customwas evaporated in vacuo
  9. customto give a yellowish oil that

Sources & evidence

ORD record
ord-fd8b6220356b4d888a630846268d0d7a
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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