Hydrochloric Acid → Ethyl 5,6,7,8-tetrahydro-5-[[2-(2-hydroxyphenyl)ethyl]amino]-2-quinolinecarboxylate

HRID 875308Notes

Reaction equation

HRID 875308 reaction equation
[CH2:1](O)[CH3:2].Cl.[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][NH:14][CH:15]1[CH2:24][CH2:23][CH2:22][C:21]2[N:20]=[C:19]([C:25]([OH:27])=[O:26])[CH:18]=[CH:17][C:16]1=2.C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][NH:14][CH:15]1[CH2:24][CH2:23][CH2:22][C:21]2[N:20]=[C:19]([C:25]([O:27][CH2:1][CH3:2])=[O:26])[CH:18]=[CH:17][C:16]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 899407575,6,7,8-Tetrahydro-5-[[2-(2-hydroxyphenyl)ethyl]amino]-2-quinolinecarboxylic acid

Product 1

HCID 89940787Ethyl 5,6,7,8-tetrahydro-5-[[2-(2-hydroxyphenyl)ethyl]amino]-2-quinolinecarboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

645 ml of anhydrous ethanol and 52 ml of a 4 N solution of hydrogen chloride in dioxane were added to 25.8 g (82.59 mmol) of 5-{[2-(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. Subsequently, the organic phase was separated off, dried over sodium sulphate, filtered and concentrated to dryness. This gave 23.9 g (70.21 mmol, 85% of theory) of the target compound.

Workup

  1. temperatureunder reflux overnight
  2. customSubsequently, the organic phase was separated off
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e5f5ed359b5443eeae6ee3bd1aa0454c
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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