HCID 86744649, compound → HCID 86744648, compound

HRID 358701Notes

Reaction equation

HRID 358701 reaction equation
C([O:4][C:5]1[C:14](=[S:15])[C:13]2[C:8](=[CH:9][C:10]([CH3:16])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1)C=C>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].Cl>[OH:4][C:5]1[C:14](=[S:15])[C:13]2[C:8](=[CH:9][C:10]([CH3:16])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1

Participants

4

Reactant 1

HCID 86744649HCID 86744649, compound

Product 1

HCID 86744648HCID 86744648, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 313Hydrochloric AcidSolvent

Procedure

Tris(triphenylphosphine)rhodium chloride (0.1 g) was added to the solution of 3-allyloxy-1-methyl-7-methylthio-4-quinolone and the mixture heated under reflux for 2 days. Hydrochloric acid (5M, 20 ml) was added dropwise and the mixture heated under reflux for 2 hours. The solvent was evaporated under reduced pressure at 50° and the resultant residue extracted with aqueous sodium hydroxide (1M, 100 ml). The extract was neutralised with hydrochloric acid (5M, 20 ml) and the solid was collected by filtration. The solid was washed with water (50 ml) and dried to give the novel compound 3-hydroxy-1-methyl-7-methylthio-4quinolone, m.p. 237°.

Workup

  1. temperaturethe mixture 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 resultant residue extracted with aqueous sodium hydroxide (1M, 100 ml)
  7. filtrationthe solid was collected by filtration
  8. washThe solid was washed with water (50 ml)
  9. customdried

Sources & evidence

ORD record
ord-9a3e0ead380f49478bb2f881bd987e5d
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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