HCID 15744999, compound → HCID 15745000, compound

HRID 327440Notes

Reaction equation

HRID 327440 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>[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

4

Reactant 2

HCID 15744999HCID 15744999, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15745000HCID 15745000, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of diethyl ((1-oxopropyl)amino)(8-quinolinylmethyl)-propanedioate (17.47 g, 0.047 mol) and platnium oxide (0.72 g) in glacial acetic acid (150 mL) was hydrogenated (50 lb 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. Calcd. 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-1e769c3af38a471abad521904f35c0ed
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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