Hydrochloric Acid → HCID 20279438, compound

HRID 1248356Notes

Reaction equation

HRID 1248356 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([C:6]1[C:15]([OH:16])=[CH:14][C:9]2[C:10]([C:12]#[N:13])=[CH:11][C:8]=2[CH:7]=1)=[O:5].[OH:22]O.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([C:6]1[C:15]([OH:16])=[CH:14][C:9]2[C:10]([C:12]([NH2:13])=[O:22])=[CH:11][C:8]=2[CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 20279442HCID 20279442, compound

Product 1

HCID 20279438HCID 20279438, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 g of 4-(2,6-dichlorobenzoyl)-5-hydroxybenzocyclobutene-1-carbonitrile are dissolved in 50 ml of ethanol, the whole is cooled to 0° and, while stirring at 0°, 10 g of 30% hydrogen peroxide are added dropwise thereto. 1.0 ml of 30% sodium hydroxide solution is then added slowly dropwise thereto and stirring is carried out for 6 hours at room temperature. The whole is neutralised with 6N hydrochloric acid and extracted thoroughly by shaking with 250 ml of dichloromethane. The organic phase is dried over magnesium sulphate and concentrated to dryness by evaporation. After recrystallisation from ether/hexane, 4-(2,6-dichlorobenzoyl)-5-hydroxybenzocyclobutene-1-carboxamide is obtained having a melting point of 174°-175°.

Workup

  1. temperaturethe whole is cooled to 0°
  2. stirringstirring
  3. extractionextracted thoroughly
  4. stirringby shaking with 250 ml of dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated to dryness by evaporation
  7. customAfter recrystallisation from ether/hexane

Sources & evidence

ORD record
ord-ff5ef970487546e4aae6be86a6dd32f9
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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