Sulfuric Acid → HCID 13537991, compound

HRID 1284496Notes

Reaction equation

HRID 1284496 reaction equation
[O:1]=[C:2]1[NH:14][C:5]2[CH:6]=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[N:12][C:13]=3[C:4]=2[O:3]1.S(=O)(=O)(O)O.[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[C:20]([N:14]1[C:5]2[CH:6]=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[N:12][C:13]=3[C:4]=2[O:3][C:2]1=[O:1])(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 12798644HCID 12798644, compound

Product 1

HCID 13537991HCID 13537991, compoundYield 80%

Procedure

A suspension of 2-oxo-3H-oxazolo[4,5-h]quinoline (1.86 g, 10.0 mmol), acetic anhydride (50 ml) and sulfuric acid (0.5 ml) was refluxed overnight. The reaction was filtered and the filtrate concentrated. Methylene chloride was added and the resulting solution was washed (3×) with water, brine; dried over MgSO4 and concentrated to a solid. The solid was crystallized from ethanol to give 1.82 g (80% yield) of product. M.P. 192°-193° C.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated
  4. additionMethylene chloride was added
  5. washthe resulting solution was washed (3×) with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a solid
  8. customThe solid was crystallized from ethanol

Sources & evidence

ORD record
ord-e489365ae0e344e3b6105e8b8cb5dac2
Source dataset
uspto-grants-1986_01
Patent number
US04563463

Reaction notes

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