1-Methoxyethanol → 1-Methyl-7-benzoyloxindole

HRID 27362

Reaction equation

HRID 27362 reaction equation
Cl[C:2]1[C:10]2[C:5](=[C:6]([C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:19])[CH:3]=1.C[O:21]C(O)C>P(=O)(O)(O)O.O>[CH3:19][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][C:3]1=[O:21]

Participants

5

Reactant 2

HCID 30156371-MethoxyethanolHCID 233426753-Chloro-1-methyl-7-benzoylindole

Product 1

HCID 201894721-Methyl-7-benzoyloxindole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1004Phosphoric AcidSolvent

Procedure

A solution of 46 grams (0.17 mol) of 3-chloro-1-methyl-7-benzoylindole in 250 ml of methoxy-ethanol and 60 ml of 70% phosphoric acid was heated at reflux under a nitrogen atmosphere for 5 hours. The solution was then cooled and diluted with 1.5 liters of water. The organic materials were extracted with methylene chloride and concentrated. The concentrated extract was chromatographed on silica gel and the product eluted with isopropyl ether. The residue obtained crystallized upon standing and was recrystallized from isopropyl alcohol to give 8.9 grams of 1-methyl-7-benzoylindolin-2-one, having a m.p. of 89°-90.5° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 5 hours
  2. temperatureThe solution was then cooled
  3. extractionThe organic materials were extracted with methylene chloride
  4. concentrationconcentrated
  5. extractionThe concentrated extract
  6. customwas chromatographed on silica gel
  7. washthe product eluted with isopropyl ether
  8. customThe residue obtained
  9. customcrystallized
  10. customwas recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-6b2b40f587964fccaca9e2784d9ad6cf
Source dataset
uspto-grants-1980_09
Patent number
US04221716

Linked notes

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