Hydrochloric Acid → 6-Amino-5-chloro-3-methylbenzofuran

HRID 637689Notes

Reaction equation

HRID 637689 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[O:5][CH2:6][C:7](=O)[CH3:8].Cl>C(O)C>[NH2:1][C:2]1[C:12]([Cl:13])=[CH:11][C:10]2[C:7]([CH3:8])=[CH:6][O:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 202556581-(3-Amino-4-chlorophenoxy)-2-propanone

Product 1

HCID 202556476-Amino-5-chloro-3-methylbenzofuran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11.4 g (57 mmole) of 1-(3-amino-4-chlorophenoxy)-2-propanone, 10 ml of concentrated hydrochloric acid and 150 ml of ethanol is boiled under reflux for 14 hours and subsequently concentrated by evaporation in vacuo. Ice-water is added to the residue and the whole is rendered alkaline with 3N sodium hydroxide solution and extracted with ether. The crude product obtained after drying and concentration by evaporation of the organic phase is chromatographed over silica gel with petroleum ether/methylene chloride. Recrystallisation of the pure fractions from ether/petroleum ether yields 6-amino-5-chloro-3-methylbenzofuran having a melting point of 73°-75°.

Workup

  1. temperatureunder reflux for 14 hours
  2. concentrationsubsequently concentrated by evaporation in vacuo
  3. additionIce-water is added to the residue
  4. extractionextracted with ether
  5. customThe crude product obtained
  6. customafter drying
  7. concentrationconcentration
  8. customby evaporation of the organic phase
  9. customis chromatographed over silica gel with petroleum ether/methylene chloride
  10. customRecrystallisation of the pure fractions from ether/petroleum ether

Sources & evidence

ORD record
ord-37b17d8d4d044743838f4688dcbbaac8
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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