Methanol → HCID 12837909, compound

HRID 2402284Notes

Reaction equation

HRID 2402284 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=[O:13])[NH:3]1.OS(O)(=O)=O.[CH3:20]O>>[CH3:20][O:13][C:12](=[O:14])[CH2:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 281699(3-Oxo-2,3-dihydro-1H-isoindol-1-yl)acetic acid

Product 1

HCID 12837909HCID 12837909, compound

Procedure

To a solution of (3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetic acid (2.0 g, 10.4 mmol) in 100 mL methanol was added 2 mL conc. H2SO4 over 5 min. The mixture was stirred at room temperature for 16 h. Solvent was evaporated, the crude oil was dissolved in 200 mL EtOAc, then washed with 50 mL sat'd NaHCO3 and 2×50 mL water. The organic phase was dried (Na2SO4), filtered, and solvent was evaporated. The title compound was isolated as a yellow oil (2.1 g, 98%).

Workup

  1. customSolvent was evaporated
  2. dissolutionthe crude oil was dissolved in 200 mL EtOAc
  3. washwashed with 50 mL
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customsolvent was evaporated

Sources & evidence

ORD record
ord-323caf89f47e4651a664f15fc92a8acc
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

Loading…