Sodium Hydroxide → HCID 58032207, compound

HRID 1629675Notes

Reaction equation

HRID 1629675 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]CC)=[O:23])=[CH:18][CH:17]=2)[CH2:6][CH:5]1[CH3:27])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)[CH2:6][CH:5]1[CH3:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66625638HCID 66625638, compound

Product 1

HCID 58032207HCID 58032207, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[Step 2] 500 mg of the crude product of 1-acetyl-4-[(4-ethoxycarbonylphenyl)amino]-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 1.5 mL of ethanol, and 0.5 mL of a 4 N aqueous solution of sodium hydroxide was added to the solution under ice cooling. The mixture was stirred for 6 hours at room temperature, and then was stirred for 6.5 hours at 60° C. After completion of the reaction, the reaction liquid was washed with diethyl ether, and was adjusted to pH 6 with a 1 N aqueous solution of hydrochloric acid. Subsequently, the reaction liquid was extracted three times with chloroform. The extraction product was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. Thus, 160 mg (cis:trans=3:1, 87%) of 1-acetyl-4-[(4-carboxyphenyl)amino]-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a yellow solid.

Workup

  1. stirringwas stirred for 6.5 hours at 60° C
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. washwas washed with diethyl ether
  5. customSubsequently, the reaction liquid
  6. extractionwas extracted three times with chloroform
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-254ade4f3a7245e28807318ebbbea804
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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