Dichloromethane → 4-Hydroxy-2-(trifluoromethyl)quinoline-3-carboxylic acid

HRID 469938Notes

Reaction equation

HRID 469938 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:17]([F:20])([F:19])[F:18])=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.ClCCl>[OH-].[Na+]>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:17]([F:20])([F:18])[F:19])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178469125HCID 178469125, compound

Product 1

HCID 1785245364-Hydroxy-2-(trifluoromethyl)quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 4-hydroxy-2-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (5 g, 17.5 mmol) in 10% aqueous NaOH solution was heated at reflux for 2 h. After cooling, dichloromethane was added and the aqueous phase was separated and acidified with concentrated HCl to pH 4. The resulting precipitate was collected via filtration, washed with water and Et2O to provide 4-hydroxy-2-trifluoromethyl-quinoline-3-carboxylic acid (A-15) (3.6 g, 80%). 1H NMR (DMSO-d6) δ 8.18-8.21 (d, J=7.8 Hz, 1 H), 7.92-7.94 (d, J=8.4 Hz, 1 H), 7.79-7.83 (t, J=14.4 Hz, 1 H), 7.50-7.53 (t, J=15 Hz, 1 H); ESI-MS 257.0 m/z (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. customthe aqueous phase was separated
  5. filtrationThe resulting precipitate was collected via filtration
  6. washwashed with water and Et2O

Sources & evidence

ORD record
ord-39049b7b328f48c1babaa76e68bcba26
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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