Water → HCID 66626015, compound

HRID 1629670Notes

Reaction equation

HRID 1629670 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[CH:7]([O:15]C(=O)C)[CH2:6][CH:5]1[CH3:19])(=[O:3])[CH3:2].[OH-].[Na+].O>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[C@@H:7]([OH:15])[CH2:6][C@@H:5]1[CH3:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66625866HCID 66625866, compound

Product 1

HCID 66626015HCID 66626015, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 3) 1.4 g of 1-acetyl-7-fluoro-4-acetoxy-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 10 mL of ethanol, and 10 mL of a 1 N aqueous solution of sodium hydroxide was added to the solution. The mixture was stirred for 1.5 hours. After completion of the reaction, water was added to the reaction liquid, and the mixture was extracted with chloroform. Subsequently, the organic layer was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (ethyl acetate:hexane=1:1), and thus 400 mg (34%) of trans-1-acetyl-7-fluoro-4-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a white solid.

Workup

  1. additionwas added to the reaction liquid
  2. extractionthe mixture was extracted with chloroform
  3. concentrationwas concentrated under reduced pressure
  4. customThe resulting residue was purified

Sources & evidence

ORD record
ord-54106d34890846f28342fab96b36a5d7
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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