HCID 86683031, compound → HCID 86683030, compound

HRID 1497209Notes

Reaction equation

HRID 1497209 reaction equation
C([O:5][C:6]([C:8]1[C:9]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)=[CH:15][C:14]([Cl:25])=[CH:13][CH:12]=2)=[O:7])(C)(C)C>Cl.O1CCOCC1>[Cl:25][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:26]([CH2:27][CH3:28])[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]([Cl:24])[CH:19]=1

Participants

4

Reactant 1

HCID 86683031HCID 86683031, compound

Product 1

HCID 86683030HCID 86683030, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-chloro-4-(3-chloro-phenyl)-2-diethylamino-quinoline-3-carboxylic acid tert-butyl ester (60 mg, 0.13 mmol) in 3 ml of 4M HCl solution in dioxane was heated to reflux and stirred for 4 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was diluted with ethyl acetate (25 ml) and washed with brine (5 ml). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to yield 6-chloro-4-(3-chloro-phenyl)-2-diethylamino-quinoline-3-carboxylic acid (45 mg, 86%) as a pale yellow solid. LC-MS (ESI): 389 (M+H)+.

Workup

  1. temperatureto reflux
  2. concentrationconcentrated in vacuo
  3. additionThe crude residue was diluted with ethyl acetate (25 ml)
  4. washwashed with brine (5 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a9f8398e40b49a79bfbfd5c51b70e28
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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