Hydrochloric Acid → 3-Quinolinecarboxylic acid, 6-bromo-4-(((2S)-2-methoxypropyl)amino)-

HRID 244596Notes

Reaction equation

HRID 244596 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16]CC)=[O:15])=[C:7]2[NH:19][CH2:20][C@@H:21]([O:23][CH3:24])[CH3:22].Cl>O.O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([OH:16])=[O:15])=[C:7]2[NH:19][CH2:20][C@@H:21]([O:23][CH3:24])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68108432ethyl 6-bromo-4-[[(2S)-2-methoxypropyl]amino]quinoline-3-carboxylate

Product 1

HCID 681075623-Quinolinecarboxylic acid, 6-bromo-4-(((2S)-2-methoxypropyl)amino)-Yield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Add a solution of sodium hydroxide (296.7 g, 7.42 mol, 6 eq.) in water (454 mL) to a solution of ethyl 6-bromo-4[[(2S)-2-methoxypropyl]amino]quinoline-3-carboxylate (454 g, 1.24 mol) in tetrahydrofuran (4.54 L) at room temperature. Heat the mixture at 50° C. overnight. After 18 hours, cool the reaction to 0° C., add 37% aq. HCl dropwise over 30 minutes until pH=6 (ca. 450 mL) with the temperature under 23° C. Filter the precipitate formed with filter paper and wash it with water (2 L), acetone (2 L) and methyl tert-butyl ether (2 L) subsequently. Dry the white solid to give the titled compound (359 g, 86%). MS (ESI) m/z (M+H)+ 338.9, 340.9.

Workup

  1. temperaturecool
  2. customthe reaction to 0° C.
  3. filtrationFilter the precipitate
  4. customformed
  5. filtrationwith filter paper
  6. washwash it with water (2 L), acetone (2 L) and methyl tert-butyl ether (2 L) subsequently
  7. customDry the white solid

Sources & evidence

ORD record
ord-62cf9a8b6aa940fc8d45db2d2f168719
Source dataset
uspto-grants-2014_02
Patent number
US08658668B2

Reaction notes

Loading…