Methanol → HCID 54412035, compound

HRID 1376795Notes

Reaction equation

HRID 1376795 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:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([OH:3])=[O:2].[CH3:24]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:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([O:3][CH3:24])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 86751207HCID 86751207, compound

Product 1

HCID 54412035HCID 54412035, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-carboxy-3-[(7-azaindol-3-yl)methylene]-2-oxindole (3.053 g, 10 mmol), methanol (3.2 g, 0.1 mol) 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-e38caa53b7f44e56917b6b43d4dd6dec
Source dataset
uspto-grants-1997_09
Patent number
US05663346

Reaction notes

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