Acetic Acid → 7-Benzoyl-5-chloroindoline

HRID 267237Notes

Reaction equation

HRID 267237 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=C(C)[N:7]3[CH2:6][CH2:5]2)[CH:10]=1.C(O)(=[O:22])C.O=[O+][O-]>O>[C:11]([C:9]1[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]2[C:8]=1[NH:7][CH2:6][CH2:5]2)(=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24823OzoneHCID 215559787-Chloro-1,2-dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole

Product 1

HCID 215559797-Benzoyl-5-chloroindoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 5 g. (0.0187 mole) of 7-chloro-1,2-dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole in 400 ml. of glacial acetic acid was treated with ozone at room temperature until all the suspended material went into solution, the reaction mixture was poured into water and the mixture extracted with chloroform. The chloroform extracts were combined and concentrated to an oil. The oil was treated with a solution of 100 ml. of hydrochloric acid and 100 ml. of glacial acetic acid; the mixture was refluxed four hours and then poured into water. The solution was extracted with chloroform, the solution dried and concentrated to an oil. The oil was dissolved in benzene and chromatographed on 50 g. of magnesium silicate. The material was molecularly distilled to give 1.5 g. (33%) of product. The yellow product melted at 114°-117°C.

Workup

  1. additionA suspension of 5 g
  2. extractionthe mixture extracted with chloroform
  3. concentrationconcentrated to an oil
  4. additionThe oil was treated with a solution of 100 ml
  5. temperaturethe mixture was refluxed four hours
  6. additionpoured into water
  7. extractionThe solution was extracted with chloroform
  8. customthe solution dried
  9. concentrationconcentrated to an oil
  10. dissolutionThe oil was dissolved in benzene
  11. customchromatographed on 50 g
  12. distillationThe material was molecularly distilled
  13. customto give 1.5 g

Sources & evidence

ORD record
ord-f987078189e148c6bbfbb62edc30672a
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

Loading…