Sulfuric Acid → HCID 21584333, compound

HRID 583234Notes

Reaction equation

HRID 583234 reaction equation
[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]2OC(=O)C(=O)[N:4]12)[CH3:2].S(=O)(=O)(O)O>CO>[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21584306HCID 21584306, compound

Product 1

HCID 21584333HCID 21584333, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-ethyl-5,9b-dihydro-4H-1-oxa-3a-aza-cyclopenta[a]naphthalene-2,3-dione (29.4 g, 0.12 mols) in methanol (1140 ml) was added concentrated sulfuric acid (60 ml) slowly. The reaction was then refluxed for 2 h. The solvent was evaporated and to the residue was added water (100 ml) and ethyl acetate (500 ml). The layers were then separated and the organic phase was then extracted with 2N HCl (2×200 ml). The aqueous layers were combined and made basic with concentrated ammonium hydroxide. The product was then extracted into dichloromethane and dried over magnesium sulfate. Evaporation of the solvent yielded 20.5 g.

Workup

  1. temperatureThe reaction was then refluxed for 2 h
  2. customThe solvent was evaporated and to the residue
  3. additionwas added water (100 ml) and ethyl acetate (500 ml)
  4. customThe layers were then separated
  5. extractionthe organic phase was then extracted with 2N HCl (2×200 ml)
  6. extractionThe product was then extracted into dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent
  9. customyielded 20.5 g

Sources & evidence

ORD record
ord-dd7c6688a8134e0c9c8378aebb482569
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

Loading…