Hydrochloric Acid → HCID 178467386, compound

HRID 1153791Notes

Reaction equation

HRID 1153791 reaction equation
C([O:4][CH:5]([C:7]1[C:16]([C:17]([NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:18])=[C:15]([OH:25])[C:14]2[C:9](=[C:10]([C:26]([F:29])([F:28])[F:27])[CH:11]=[CH:12][CH:13]=2)[N:8]=1)[CH3:6])(=O)C.Cl>C(O)C>[OH:25][C:15]1[C:14]2[C:9](=[C:10]([C:26]([F:27])([F:29])[F:28])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([CH:5]([OH:4])[CH3:6])[C:16]=1[C:17]([NH:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1)=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178476200HCID 178476200, compound

Product 1

HCID 178467386HCID 178467386, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.3 g of the product of Example 1, 50 ml of ethanol and 25 ml of concentrated hydrochloric acid was refluxed with stirring for one hour and was then cooled and iced and vacuum filtered. The product was washed and dried under reduced pressure at 60° C. The said product was added to 300 ml of water and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was crystallized from ethyl acetate. The mixture was iced and vacuum filtered and the recovered product was washed and dried under reduced pressure at 60° C. to obtain 2.45 g of 4-hydroxy-2-(1-hydroxyethyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 205° C. and then at 235° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewas then cooled
  3. filtrationiced and vacuum filtered
  4. washThe product was washed
  5. customdried under reduced pressure at 60° C
  6. additionThe said product was added to 300 ml of water
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic phase was washed with water
  9. customdried
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness under reduced pressure
  12. customthe residue was crystallized from ethyl acetate
  13. filtrationvacuum filtered
  14. washthe recovered product was washed
  15. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-ae47272ed8db4c668d954d52bf196ed6
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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