HCID 13548560, compound → HCID 14873016, compound

HRID 703444Notes

Reaction equation

HRID 703444 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1>CO.C1(C)C=CC=CC=1.[Pt]=O>[O:1]=[C:2]1[CH2:11][CH:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 1

HCID 13548560HCID 13548560, compound

Product 1

HCID 14873016HCID 14873016, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

50 g (0.23 mol) of methyl 2-oxo-1,2-dihydro-4-quinolinacetate dissolved in 1 l of methanol is subjected to hydrogenation in a Parr apparatus in the presence of 2 g of Adams' platinum oxide under 40 to 45 psi and at 60° C. for approximately 1 h. After the catalyst is filtered off and the solvent evaporated off, the oily residue is chromatographed on silica. Elution with a dichloromethane/acetone (95:5) mixture yields an oil, which is solubilized in 250 ml of boiling toluene. After being cooled, this solution is diluted with 250 ml of petroleum ether. The crystalline product thereby obtained is drained, washed and dried. 36.8 g (73%) of methyl (±)-2-oxo-1,2,3,4-tetrahydro-4-quinolineacetate, melting point 115°-116° C., are obtained.

Workup

  1. filtrationAfter the catalyst is filtered off
  2. customthe solvent evaporated off
  3. customthe oily residue is chromatographed on silica
  4. washElution with a dichloromethane/acetone (95:5) mixture
  5. customyields an oil, which
  6. temperatureAfter being cooled
  7. customThe crystalline product thereby obtained
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-f16fcebe68ed490c84eb86b7ae432258
Source dataset
uspto-grants-1991_01
Patent number
US04983607

Reaction notes

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