Hydrochloric Acid → HCID 21474339, compound

HRID 2294257Notes

Reaction equation

HRID 2294257 reaction equation
Cl.C([O:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:12]([CH2:17][CH2:18]O)[C:11]=1[CH:20]([OH:28])[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)C1C=CC=CC=1.[OH-].[Na+]>C(OCC)(=O)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH:20]2[C:11]3=[C:10]([OH:9])[C:15](=[O:16])[CH:14]=[CH:13][N:12]3[CH2:17][CH2:18][O:28]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21474316HCID 21474316, compound

Product 1

HCID 21474339HCID 21474339, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

2.5 ml of 37% conc. hydrochloric acid are added to 0.245 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[hydroxy-(4-chloro-phenyl)-methyl]-1H-pyridin-4-one (Example 34e) and the solution is heated with stirring at 110° C. for 45 minutes. After cooling, 5 g of ice are added. The reaction mixture is neutralised with sodium hydroxide solution to a pH of 6.5, then 5 ml of ethyl acetate are added and stirring is carried out for 4 hours in an ice-bath. The reaction mixture is filtered and washed with water and ethyl acetate. Drying yields 1-(4-chloro-phenyl)-9-hydroxy-3,4-dihydro-1H-pyrido[2,1-c][1,4]oxazin-8-one. Pink crystals, m.p.: 211°-214° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureAfter cooling
  3. stirringstirring
  4. waitis carried out for 4 hours in an ice-bath
  5. filtrationThe reaction mixture is filtered
  6. washwashed with water and ethyl acetate
  7. customDrying

Sources & evidence

ORD record
ord-4e7e871c905e490bb2fe6f1d4cfdf227
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

Loading…