Water → HCID 178519483, compound

HRID 596795Notes

Reaction equation

HRID 596795 reaction equation
[C:1]([C:9]1[C:18]([CH2:19]Br)=[N+:17]([O-:21])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N+:10]=1[O-:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:23]>>[C:1]([C:9]1[C:18]([CH2:19][OH:23])=[N+:17]([O-:21])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N+:10]=1[O-:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 962WaterHCID 178519460HCID 178519460, compound

Product 1

HCID 178519483HCID 178519483, compoundYield 59%

Conditions

Temperature
25 °C

Procedure

A stirred slurry of 10.0 g (0.028 mol.) of 2-benzoyl-3-bromomethylquinoxaline 1,4-dioxide in 1,000 ml. of water was heated under reflux for 18 hours. The hot reaction mixture was filtered, and the filtrate was allowed to cool to 25° C. The solid which precipitated was collected by filtration to provide a first crop of crude product. The aqueous filtrate was extracted with dichloromethane, which was then dried and evaporated in vacuo, to provide a second crop of crude product. The combined crude product was 7.0 g. (85% yield). It was recrystallized from ethanol to give 4.9 g. (59% yield) of 2-benzoyl-3-hydroxymethylquinoxaline 1,4-dioxide having m.p 178°-179° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. filtrationThe hot reaction mixture was filtered
  3. customThe solid which precipitated
  4. filtrationwas collected by filtration
  5. customto provide a first crop of crude product
  6. extractionThe aqueous filtrate was extracted with dichloromethane, which
  7. customwas then dried
  8. customevaporated in vacuo
  9. customto provide a second crop of crude product
  10. customIt was recrystallized from ethanol
  11. customto give 4.9 g

Sources & evidence

ORD record
ord-f2fbf1e1a5084e809ecea5faf3577f9f
Source dataset
uspto-grants-1977_03
Patent number
US04012385

Reaction notes

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