Hydrochloric Acid → HCID 21474385, compound

HRID 2294255Notes

Reaction equation

HRID 2294255 reaction equation
Cl.C([O:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:12]([CH2:17][CH2:18][OH:19])[C:11]=1[CH:20]([OH:28])[C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)C1C=CC=CC=1.[OH-].[Na+]>C(OCC)(=O)C>[Br:27][C:24]1[CH:23]=[CH:22][C:21]([CH:20]([OH:28])[C:11]2[N:12]([CH2:17][CH2:18][OH:19])[CH:13]=[CH:14][C:15](=[O:16])[C:10]=2[OH:9])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21474445HCID 21474445, compound

Product 1

HCID 21474385HCID 21474385, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

12 ml of 37% conc. HCl are poured over 1.2 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[hydroxy-(4-bromo-phenyl)-methyl]-1H-pyridin-4-one and the reaction mixture is heated with stirring at 110° C. for 10 minutes. After cooling, 15 g of ice are added. With stirring and cooling in an ice bath, the reaction mixture is neutralised with sodium hydroxide solution to a pH of 6.5. 15 ml of ethyl acetate are added and stirring is carried out at room temperature for 18 hours. The resulting product is filtered off and washed with water and ethyl acetate. Recrystallisation from ethanol yields 2-[(4-bromo-phenyl)-hydroxy-methyl]-3-hydroxy-1-(2-hydroxy-ethyl)-1H-pyridin-4-one.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureAfter cooling
  3. stirringWith stirring
  4. temperaturecooling in an ice bath
  5. stirringstirring
  6. waitis carried out at room temperature for 18 hours
  7. filtrationThe resulting product is filtered off
  8. washwashed with water and ethyl acetate
  9. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-c49ac37788864c4ca366a8e715a2ec7a
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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