Hydrochloric Acid → HCID 23369675, compound

HRID 1900735Notes

Reaction equation

HRID 1900735 reaction equation
O[C:2]1[C:11]([CH:12]([CH:15]=[CH2:16])[CH2:13][OH:14])=[CH:10][C:9]([CH3:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:18])[NH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.Cl>N1C=CC=CC=1.CO>[CH3:17][C:9]1[CH:10]=[C:11]2[CH:12]([CH:15]=[CH2:16])[CH2:13][O:14][C:2]2=[C:3]2[C:8]=1[NH:7][C:6](=[O:18])[CH:5]=[CH:4]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 23369638HCID 23369638, compound

Product 1

HCID 23369675HCID 23369675, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

5-Hydroxy-6-(2-hydroxy-1-vinylethyl)-8methylcarbostyril (7.2 g) was dissolved in pyridine (50 ml), to which triphenylphosphine (25.0 g) and carbon tetrachloride (15 ml) were added in this order, followed by stirring at 60° C. for 3 hours. Methanol (50 ml) was added thereto and stirred for 1 hour. The reaction mixture was filtered. The filtrate was condensed under reduced pressure, to which 1N-HCl was added. Extraction was performed with chloroform. The chloroform phase was dried, and the solvent was evaporated. The residue was recrystallized from a solvent mixture of chloroform-ethyl acetate-ether to obtain 6.4 g of 5-methyl-2,3,6,7-tetrahydro-3-vinylfuro[2,3-f]quinoline-7-one as colorless powdery crystals (95.9%).

Workup

  1. additionwere added in this order
  2. stirringstirred for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. customcondensed under reduced pressure
  5. extractionExtraction
  6. dry with materialThe chloroform phase was dried
  7. customthe solvent was evaporated
  8. customThe residue was recrystallized from a solvent mixture of chloroform-ethyl acetate-ether

Sources & evidence

ORD record
ord-ad58cdeedd714159bac65ecf8a696c76
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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