Hydrochloric Acid → (5-Chloro-6-quinolinyl)methanol

HRID 581999Notes

Reaction equation

HRID 581999 reaction equation
CO[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:13](C3C=CC=C(C(F)(F)F)C=3)[OH:14])[CH:9]=2)[N:4]=1.[ClH:25].[OH-].[Na+]>>[Cl:25][C:9]1[C:8]([CH2:13][OH:14])=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][CH:3]=[N:4]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54187627(+/-)-2-Methoxy-alpha-[3-(trifluoromethyl)phenyl]-6-quinoline methanol

Product 1

HCID 45588508(5-Chloro-6-quinolinyl)methanol

Procedure

A mixture of intermediate 28 (1 g) and HCl (25 ml; 3 N) was stirred and refluxed for 2 hours. The solution was basified with NaOH and extracted with CH2Cl2. The organic layer was separated, washed with brine, dried over MgSO4, filtered and the solvent was evaporated, yielding 1.8 g of (±)-6-[hydroxy[3-(trifluoromethyl)phenyl]methyl]-2(1H-quinolinone (intermediate 29).

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b1e413b95cdf4556be0200fb3f8e4c58
Source dataset
uspto-grants-1999_07
Patent number
US05922734

Reaction notes

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