Hydrochloric Acid → HCID 23128113, compound

HRID 358699Notes

Reaction equation

HRID 358699 reaction equation
C([O:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([C:16]#[N:17])=[CH:11][CH:12]=2)[N:7]([CH3:18])[CH:6]=1)C=C.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].C(O)C>[C:16]([C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:15])[C:5]([OH:4])=[CH:6][N:7]2[CH3:18])=[CH:12][CH:11]=1)#[N:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23128075HCID 23128075, compound

Product 1

HCID 23128113HCID 23128113, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolvent

Procedure

A mixture of the crude 3-allyloxy-7-cyano-1-methyl-4-quinolone (1.2 g), tris(triphenylphosphine)rhodium chloride (0.1 g) and ethanol (200 ml) was heated under reflux for 2 days. Hydrochloric acid (1M, 10 ml) was added, the mixture heated under reflux for 2 hours and then the solvent was evaporated under reduced pressure at 50°. The residue was extracted with aqueous sodium hydroxide (1M, 50 ml) and the extract neutralised with hydrochloric acid (12M, 4 ml). The resultant solid was collected by filtration and washed with water (10 ml) t give the novel compound 7-cyano-3-hydroxy-1-methyl-4-quinolone, m.p. 305°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 2 hours
  5. customthe solvent was evaporated under reduced pressure at 50°
  6. extractionThe residue was extracted with aqueous sodium hydroxide (1M, 50 ml)
  7. filtrationThe resultant solid was collected by filtration
  8. washwashed with water (10 ml) t

Sources & evidence

ORD record
ord-adc45341d9d84a3d98a2e98045c43f8d
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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