Hydrochloric Acid → HCID 71556884, compound

HRID 1497174Notes

Reaction equation

HRID 1497174 reaction equation
C([O:5][C:6]([C:8]1[C:9]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[CH:19]=1)=[CH:15][C:14]([Cl:27])=[CH:13][CH:12]=2)=[O:7])(C)(C)C.Cl>O1CCOCC1.CCOC(C)=O>[Cl:27][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:8]([C:6]([OH:7])=[O:5])=[C:17]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86683007HCID 86683007, compound

Product 1

HCID 71556884HCID 71556884, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To 6-chloro-2-diethylamino-4-(3-isopropyl-phenyl)-quinoline-3-carboxylic acid tert-butyl ester (75 mg, 0.17 mmol) was added a solution of HCl in dioxane (4N, 3 ml), and the mixture was heated to reflux for 4 h. The reaction mixture was then cooled to room temperature and then concentrated in vacuo to give a crude residue which was diluted with EtOAc (20 ml). The organic layer was washed with brine (10 ml), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford 6-chloro-2-diethylamino-4-(3-isopropyl-phenyl)-quinoline-3-carboxylic acid (55 mg, 84%) as a pale yellow solid. LC-MS (ESI): 397 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated in vacuo
  4. customto give a crude residue which
  5. washThe organic layer was washed with brine (10 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d6b76c7532943b3bd7f6d3717f1cfe5
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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