Hydrochloric Acid → HCID 20329649, compound

HRID 2057975Notes

Reaction equation

HRID 2057975 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:15]=3[CH:24]=2)=[CH:7][CH:6]=1)(=O)C.Cl>C(O)C>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:15]=3[CH:24]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20329641HCID 20329641, compound

Product 1

HCID 20329649HCID 20329649, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g of 12B, 50 ml of 6 N hydrochloric acid and 50 ml of ethanol was stirred and refluxed for 5 hours. The solution was concentrated to about half its volume, the solid that formed was collected, and dissolved in chloroform containing some triethylamine. The solution was washed with water, dried (MgSO4) and filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was dry column chromatographed over silica gel, using a 1/9 v/v mixture of tetrahydrofuran and chloroform as eluent. The solvents were evaporated, the appropriate sections were combined and extracted with chloroform. The extract was filtered and the solvent was evaporated under reduced pressure. The residue was refluxed in petroleum ether for 8 hours. The mixture was filtered and the filtrate placed in a freezer overnight. The solid that formed was collected and dried to give ethyl 5-(4-aminophenyl)benzofuran-2-carboxylate (12C), mp: 95°-97° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. concentrationThe solution was concentrated to about half its volume
  3. customthe solid that formed
  4. customwas collected
  5. dissolutiondissolved in chloroform containing some triethylamine
  6. washThe solution was washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe solvent was evaporated from the filtrate under reduced pressure
  10. customThe residue was dry column
  11. customchromatographed over silica gel
  12. additiona 1/9 v/v mixture of tetrahydrofuran and chloroform as eluent
  13. customThe solvents were evaporated
  14. extractionextracted with chloroform
  15. filtrationThe extract was filtered
  16. customthe solvent was evaporated under reduced pressure
  17. temperatureThe residue was refluxed in petroleum ether for 8 hours
  18. filtrationThe mixture was filtered
  19. customThe solid that formed
  20. customwas collected
  21. customdried

Sources & evidence

ORD record
ord-746f6ef67af34d73aeafb5c319f6c1fb
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Reaction notes

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