Sulfuric Acid → octahydro-3-oxo-1H-isoindole-1-carboxylic acid

HRID 2164220Notes

Reaction equation

HRID 2164220 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]([OH:13])=[O:12])[NH:3]1.S(=O)(=O)(O)O>C(O)C>[O:1]=[C:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH:4]([C:11]([OH:13])=[O:12])[NH:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 97940173-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acid

Product 1

HCID 13388635octahydro-3-oxo-1H-isoindole-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The intermediate octahydro-3-oxo-1H-isoindole-1-carboxylic acid is prepared as follows. 2,3-Dihydro-3-oxo-1H-isoindole-1-carboxylic acid (J. Prakt. Chem., 146, 307(1936)), 20 g is heated at reflux for 2 hours with 250 ml of absolute ethanol and 5.6 g of concentrated sulfuric acid. On cooling, the solution deposits crystalline ethyl 2,3-dihydro-3-oxo-1H-isoindole-3-carboxylate. Recrystallization of this from ethanol gives pure material, mp 178°-183° C.

Workup

  1. temperatureOn cooling
  2. customRecrystallization of this from ethanol
  3. customgives pure material, mp 178°-183° C.

Sources & evidence

ORD record
ord-85603dea77a546838d4bf959cc06563e
Source dataset
uspto-grants-1985_03
Patent number
US04503043

Reaction notes

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