Diethyl ((1-oxopropyl)amino)(8-quinolinylmethyl)propanedioate → HCID 15745000, compound

HRID 1648283Notes

Reaction equation

HRID 1648283 reaction equation
[O:1]=[C:2]([NH:5][C:6]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[CH:25][CH:24]=[CH:23]2)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9]CC)=O)[CH2:3][CH3:4].[H][H]>C(O)(=O)C.[Pt]=O>[O:9]=[C:7]1[C:6]([NH:5][C:2](=[O:1])[CH2:3][CH3:4])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:17][C:18]2=[CH:19][CH:20]=[CH:21][C:22]3=[C:27]2[N:26]1[CH2:25][CH2:24][CH2:23]3

Participants

5

Reactant 2

HCID 15744999Diethyl ((1-oxopropyl)amino)(8-quinolinylmethyl)propanedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 15745000HCID 15745000, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of diethyl ((1-oxopropyl)amino)(8-quinolinylmethyl)propanedioate (17.47 g, 0.047 mol) and platinum oxide (0.72 g) in glacial acetic acid (150 mL) was hydrogenated (50 1b initial pressure) until hydrogen uptake ceased (1.8 equiv). The mixture was filtered through celite and the solvent removed under reduced pressure. The product was crystallized from ethyl acetate to give 12.08 g of crystals, mp 136°-140° C. A sample was recrystallized from ethyl acetate for analysis; mp 137°-141° C. Anal. Calc'd for C18H22N2O4 : C, 65.44; H, 6.71; N, 8.48. Found: C, 65.66; H, 6.64; N, 8.43.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent removed under reduced pressure
  3. customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e08e414bbe2a45dbb3459ecee4080ce7
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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