Hydrochloric Acid → HCID 21474402, compound

HRID 2294266Notes

Reaction equation

HRID 2294266 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17]O)[C:10]=1[CH:19]([OH:28])[C:20]1[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=1)C1C=CC=CC=1.C(OCC)(=O)C.[OH-].[Na+].[ClH:37]>>[ClH:37].[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]2[CH2:16][CH2:17][O:28][CH:19]([C:20]3[CH:21]=[CH:22][C:23]([S:26][CH3:27])=[CH:24][CH:25]=3)[C:10]=12

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21474415HCID 21474415, compound

Product 1

HCID 21474402HCID 21474402, compound

Procedure

5.99 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[hydroxy-(4-methylthio-phenyl)-methyl]-1H-pyridin-4-one are boiled under reflux for 45 minutes in 60 ml of 6N hydrochloric acid. The reaction mixture is cooled to room temperature and covered with 10 ml of ethyl acetate. With vigorous stirring, the reaction mixture is neutralised with dilute sodium hydroxide solution until the product precipitates in the form of crystals. The reaction mixture is left to stand overnight in a refrigerator and then filtered. The crystals are washed with a small amount of cold alcohol. Drying yields 9-hydroxy-1-(4-methylthio-phenyl)-3,4-dihydro-1H-pyrido[2,1-c]-[1,4]oxazin-8-one hydrochloride, M.p.: 235°-238° C.

Workup

  1. customprecipitates in the form of crystals
  2. waitThe reaction mixture is left
  3. filtrationfiltered
  4. washThe crystals are washed with a small amount of cold alcohol
  5. customDrying

Sources & evidence

ORD record
ord-ce3745c9990e410093efc000e15ca98f
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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