Trifluoroacetic acid → 6-Chloro-4-(3-chloro-phenyl)-2-isopropoxy-quinoline-3-carboxylic acid

HRID 1497221Notes

Reaction equation

HRID 1497221 reaction equation
C([O:5][C:6]([C:8]1[C:9]([O:26][CH:27]([CH3:29])[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.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:26][CH:27]([CH3:28])[CH3:29])[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 2

HCID 6422Trifluoroacetic acidHCID 866830426-Chloro-4-(3-chloro-phenyl)-2-isopropoxy-quinoline-3-carboxylic acid tert-butyl ester

Product 1

HCID 715560526-Chloro-4-(3-chloro-phenyl)-2-isopropoxy-quinoline-3-carboxylic acidYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of 6-chloro-4-(3-chloro-phenyl)-2-isopropoxy-quinoline-3-carboxylic acid tert-butyl ester (100 mg, 0.23 mmol) in DCM (4 ml) was added 0.2 ml TFA and reaction mixture was refluxed for 16 h. After cooling, the volatiles were removed under vacuum and the reaction mixture was diluted with ethyl acetate (40 ml) and washed with NaHCO3 solution (10 ml). The separated organic layer was washed with brine (7 ml), dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (100% ethyl acetate) to afford 6-chloro-4-(3-chloro-phenyl)-2-isopropoxy-quinoline-3-carboxylic acid (14 mg, 16%) as an off white solid. LC-MS (ESI): 374 (M−H)−.

Workup

  1. temperaturewas refluxed for 16 h
  2. temperatureAfter cooling
  3. customthe volatiles were removed under vacuum
  4. additionthe reaction mixture was diluted with ethyl acetate (40 ml)
  5. washwashed with NaHCO3 solution (10 ml)
  6. washThe separated organic layer was washed with brine (7 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a crude residue which
  10. customwas purified by flash column chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-77a2795a995f4f4683c50525446e7965
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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