Benzoyl chloride → 7-Benzoyl-5-chloro-1,3-dihydro-2H-indol-2-one

HRID 1704318Notes

Reaction equation

HRID 1704318 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH2:18]2>CO>[C:1]([C:22]1[CH:23]=[C:15]([Cl:14])[CH:16]=[C:17]2[C:21]=1[NH:20][C:19](=[O:24])[CH2:18]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 1528015-ChlorooxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 129012237-Benzoyl-5-chloro-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 162.5 g. (1.08 mole) of benzoyl chloride and 260 g. of aluminum chloride (1.80 mole) heated to 200° C. with stirring was treated with 65 g. (0.360 mole) of recrystallized 5-chloroindolin-2-one. This mixture was stirred 15 min. and poured over ice. The resulting precipitate was triturated with boiling water and then chloroform. The chloroform solution was washed with 5% sodium bicarbonate, water, dried over sodium sulfate, and stripped to yield approximately 55 g. of a glossy solid. This material was then triturated with hot methanol and the methanol evaporated under vacuum to yield approximately 20 g. of a solid yellow material. Extraction of a benzene solution of this material removed any starting 5-chloroindoline-2-one present and after washing with water and drying the benzene yielded on evaporation 3 g. of a blue-gray material. Trituration of this material with room temperature methanol gave a residue which on recrystallization from methanol yielded 2.5 g. of a tan solid identified as product, m.p. 186°-187° C.

Workup

  1. additionA mixture of 162.5 g
  2. additionwas treated with 65 g
  3. stirringThis mixture was stirred 15 min.
  4. additionpoured over ice
  5. customThe resulting precipitate was triturated with boiling water
  6. washThe chloroform solution was washed with 5% sodium bicarbonate, water
  7. dry with materialdried over sodium sulfate
  8. customto yield approximately 55 g
  9. customThis material was then triturated with hot methanol
  10. customthe methanol evaporated under vacuum
  11. customto yield approximately 20 g
  12. extractionExtraction of a benzene solution of this material
  13. customremoved any starting 5-chloroindoline-2-one present
  14. washafter washing with water
  15. dry with materialdrying the benzene
  16. customyielded on evaporation 3 g
  17. customon recrystallization from methanol
  18. customyielded 2.5 g

Sources & evidence

ORD record
ord-1630e62f12e843a9b8af0154acfee7cd
Source dataset
uspto-grants-1978_11
Patent number
US04126635

Reaction notes

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