Methanol → HCID 70336262, compound

HRID 356998Notes

Reaction equation

HRID 356998 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[CH:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][CH:16]=1)([OH:3])=[O:2].[CH3:25]O.OS(O)(=O)=O>C1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[CH:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][CH:16]=1)([O:3][CH3:25])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70340538HCID 70340538, compound

Product 1

HCID 70336262HCID 70336262, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-carboxy-3-(quinol-4-ylmethylene)-2-oxindole (3.163 g, 10 mmol), methanol (3.2 g, 100 mmol) and H2SO4 95% (1 g) in benzene (100 ml) was heated in a Soxhlet apparatus for 10 h. To dry the distillate continuously, the cap of the Soxhlet contained anhydrous MgSO4. After cooling, water was added, the organic phase repeatedly washed with water and then evaporated under vacuum. Thus almost pure title compound was obtained in about 90% yield.

Workup

  1. customTo dry the distillate continuously
  2. customthe cap of the Soxhlet
  3. temperatureAfter cooling
  4. additionwater was added
  5. washthe organic phase repeatedly washed with water
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-b113df1d64f24ee4bb50e0169e29b6ed
Source dataset
uspto-grants-1998_11
Patent number
US05840745

Reaction notes

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