Diethyl (formylamino)(8-quinolinylmethyl)malonate → HCID 86747427, compound

HRID 327437Notes

Reaction equation

HRID 327437 reaction equation
[CH:1]([NH:3][C:4]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)([C:10](OCC)=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:2].[H][H]>C(O)(=O)C.[Pt]=O>[O:11]=[C:10]1[C:4]([NH:3][CH:1]=[O:2])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:15][C:16]2=[CH:17][CH:18]=[CH:19][C:20]3=[C:25]2[N:24]1[CH2:23][CH2:22][CH2:21]3

Participants

5

Reactant 2

HCID 54322974Diethyl (formylamino)(8-quinolinylmethyl)malonateHCID 178418361HCID 178418361, compound

Product 1

HCID 86747427HCID 86747427, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of diethyl (formylamino)(8-quinolinylmethyl)malonate (9.2 g, 26.7 mmol) and platinum oxide (0.7 g) in glacial acetic acid (150 mL) was hydrogenated (50 lb initial pressure) for 15 minutes (hydrogen uptake ca. 2 equiv). The mixture was filtered through celite and the solvent removed under reduced pressure. The product was partitioned between ethyl acetate and sodium hydroxide solution. The ethyl acetate phase was washed with water, the ethyl acetate was evaporated, and the product was crystallized from ether to give 7.8 g (97%) of ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)-1H,5H-benzo(ij)quinolizine-2-carboxylate, mp 103°-106° C. Anal. Calcd. for C16H18N2O4 : C, 63.56; H, 6.00; N, 9.27. Found: C, 63.51; H, 6.09; N, 9.18.

Workup

  1. customfor 15 minutes
  2. filtrationThe mixture was filtered through celite
  3. customthe solvent removed under reduced pressure
  4. customThe product was partitioned between ethyl acetate and sodium hydroxide solution
  5. washThe ethyl acetate phase was washed with water
  6. customthe ethyl acetate was evaporated
  7. customthe product was crystallized from ether

Sources & evidence

ORD record
ord-304c9e242c2a4b39a9fc76d7aa0fcdf5
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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