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

HRID 2404625Notes

Reaction equation

HRID 2404625 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, 1H), 7.92-7.94 (d, J=8.4 Hz, 1H), 7.79-7.83 (t, J=14.4 Hz, 1H), 7.50-7.53 (t, J=15 Hz, 1H); 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-e63b7d6f285f4fabba475b98fdbb356a
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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