Acetic Acid → HCID 10313855, compound

HRID 2260591Notes

Reaction equation

HRID 2260591 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3C(C#N)[C:6]=2[CH:18]=1.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>>[Br:1][C:2]1[CH:18]=[CH:6][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:21]([C:20]([OH:23])=[O:22])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10402506HCID 10402506, compound

Product 1

HCID 10313855HCID 10313855, compound

Procedure

A mixture of 5.48 g of 9-bromo-6,11-dihydrodibenz[b,e]oxepin-11-carbonitrile, 80 ml of conc. hydrochloric acid and 80 ml of acetic acid was heated under reflux for 15 hours. The reaction mixture was allowed to stand at room temperature. The crystals precipitated were collected by filtration and dissolved in dichloromethane. The solution was washed with water, dried and concentrated to dryness under reduced pressure. The crude crystals were recrystallized from toluene to obtain 1.83 g of Compound R.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customto stand at room temperature
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. dissolutiondissolved in dichloromethane
  7. washThe solution was washed with water
  8. customdried
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe crude crystals were recrystallized from toluene

Sources & evidence

ORD record
ord-42b8e87558a14aafa41924fee99bc5bb
Source dataset
uspto-grants-1995_12
Patent number
US05478835

Reaction notes

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