Hydrochloric Acid → HCID 66917274, compound

HRID 2388130Notes

Reaction equation

HRID 2388130 reaction equation
Cl.[F:2][C:3]1[CH:12]=[CH:11][C:10]([O:13]COC)=[C:9]2[C:4]=1[C:5](=[O:25])[C:6]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[CH:7][NH:8]2.O.[Na]>C(O)C>[F:2][C:3]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]2[C:4]=1[C:5](=[O:25])[C:6]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[CH:7][NH:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66917184HCID 66917184, compoundHCID 71353970Sodium monohydrate

Product 1

HCID 66917274HCID 66917274, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

2N Hydrochloric acid (6.0 ml) was added to an ethanol solution (18 ml) of 5-fluoro-8-methoxymethoxy-3-(4-methoxyphenyl)-1H-quinolin-4-one (350 mg, 1.06 mmol). The mixture was stirred at 55° C. for 1 hour. The stirred mixture was cooled to room temperature, and 1N sodium hydrate (11.6 ml) was added thereto to obtain a pH of 3 to 4. The mixture in which pH was adjusted was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (dichloromethane:methanol=50:1→20:1). The purified product was concentrated under reduced pressure, and the residue was crystallized from ethanol, collected by filtration, washed with ethanol, and dried to thereby obtain 165 mg of powdery pale dark brown 5-fluoro-8-hydroxy-3-(4-methoxyphenyl)-1H-quinolin-4-one (yield: 54%).

Workup

  1. temperatureThe stirred mixture was cooled to room temperature
  2. customto obtain a pH of 3 to 4
  3. concentrationThe mixture in which pH was adjusted was concentrated under reduced pressure
  4. customthe residue was then purified by silica gel column chromatography (dichloromethane:methanol=50:1→20:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customthe residue was crystallized from ethanol
  7. filtrationcollected by filtration
  8. washwashed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-0062db0299414f6bb62d785a2f45dbae
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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