Hydrochloric Acid → HCID 23128141, compound

HRID 358692Notes

Reaction equation

HRID 358692 reaction equation
C([O:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10](F)=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1)C=C.[CH3:18][O-:19].[Na+].Cl>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].CO>[OH:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([O:19][CH3:18])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 10942334Sodium MethoxideHCID 23128086HCID 23128086, compound

Product 1

HCID 23128141HCID 23128141, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-allyloxy-7-fluoro-1-methyl-4quinolone (2.1 g), prepared as described in Example 8(a), sodium methoxide (3 g) and dry methanol (50 ml) was heated under reflux for 4 days. Methanolic hydrochloric acid was added to neutralise the solution and tris(triphenylphosphine)rhodium chloride (0.2 g) was added. The mixture was heated under reflux for 3 days and then acidified with methanolic hydrochloric acid to pH 1. The solvent was removed by distillation under reduced pressure and the residue stirred with aqueous sodium hydroxide (0.5M, 50 ml) and filtered. The filtrate was neutralised with hydrochloric acid (5M, 5 ml), the precipitate was collected by filtration and washed with water (2×10 ml) to give the novel compound 3-hydroxy-7-methoxy-1-methyl-4-quinolone, m.p. 228°.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureunder reflux for 4 days
  4. additionwas added
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for 3 days
  7. customThe solvent was removed by distillation under reduced pressure
  8. filtrationfiltered
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water (2×10 ml)

Sources & evidence

ORD record
ord-ff26b19979584d19b2f0dde23e727923
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…