Hydrochloric Acid → 7-Fluoro-2-methylquinolin-3-ol

HRID 2174205Notes

Reaction equation

HRID 2174205 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.[OH-:13].[K+].Br[CH2:16][C:17](C1C=CC=CC=1)=O.Cl>O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:16]=[C:17]([OH:13])[C:7]([CH3:6])=[N:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6259Phenacyl bromideHCID 14797Potassium HydroxideHCID 3739056-Fluoroisatin

Product 1

HCID 892555517-Fluoro-2-methylquinolin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.96 g of the crude product of 6-fluoroisatin were added to 55 mL of water followed by the addition of 16.2 g (6 equivalents) of KOH while cooling with ice and stirring for 30 minutes. 9.9 g (1.5 equivalents) of bromoacetophenone were dropped into the resultant suspension while holding the internal temperature of the reaction mixture at 20° C. to 25° C. followed by additionally stirring overnight at room temperature. After neutralizing with concentrated hydrochloric acid, the precipitated crystals were filtered out and washed with a small amount of water. After adequately drying the resulting crystals, 70 mL of nitrobenzene heated to 120° C. to 130° C. were added a little at a time followed by further stirring for 1 hour at 140° C. to 150° C. After cooling the reaction mixture to room temperature, the precipitated crystals were washed with chloroform to obtain 5.4 g of 7-fluoro-3-hydroxy-2-methylquinoline.

Workup

  1. temperaturewhile cooling with ice
  2. customat 20° C. to 25° C.
  3. stirringby additionally stirring overnight at room temperature
  4. filtrationthe precipitated crystals were filtered out
  5. washwashed with a small amount of water
  6. dry with materialAfter adequately drying the resulting crystals, 70 mL of nitrobenzene
  7. temperatureheated to 120° C. to 130° C.
  8. additionwere added a little at a time
  9. stirringby further stirring for 1 hour at 140° C. to 150° C
  10. washthe precipitated crystals were washed with chloroform

Sources & evidence

ORD record
ord-3e917da5356d409eb853849db1f4a198
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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