Hydrochloric Acid → rac-Ethyl 5-{[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875329Notes

Reaction equation

HRID 875329 reaction equation
[CH2:1](O)[CH3:2].Cl.[F:5][C:6]1[CH:7]=[CH:8][C:9]([OH:28])=[C:10]([CH2:12][CH2:13][NH:14][CH:15]2[CH2:24][CH2:23][CH2:22][C:21]3[N:20]=[C:19]([C:25]([OH:27])=[O:26])[CH:18]=[CH:17][C:16]2=3)[CH:11]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[F:5][C:6]1[CH:7]=[CH:8][C:9]([OH:28])=[C:10]([CH2:12][CH2:13][NH:14][CH:15]2[CH2:24][CH2:23][CH2:22][C:21]3[N:20]=[C:19]([C:25]([O:27][CH2:1][CH3:2])=[O:26])[CH:18]=[CH:17][C:16]2=3)[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 89940808rac-5-{[2-(5-Fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

Product 1

HCID 89950549rac-Ethyl 5-{[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

40 ml of anhydrous ethanol and 4 ml of a 4 N solution of hydrogen chloride in dioxane were added to 1.93 g (5.84 mmol) of rac-5-{[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid, and the mixture was stirred under reflux overnight. The reaction solution was then cooled to room temperature, and first ethyl acetate and then, slowly, saturated aqueous sodium bicarbonate solution were added. The organic phase was separated off, dried over magnesium sulphate, filtered and concentrated to dryness. This gave 1.67 g (4.66 mmol, 80% of theory) of the target compound.

Workup

  1. temperatureunder reflux overnight
  2. customThe organic phase was separated off
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-23e6f81139c14a3cbc8ac2e452e68d7f
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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