Hydrochloric Acid → HCID 13175315, compound

HRID 2418215Notes

Reaction equation

HRID 2418215 reaction equation
[O:1]=[C:2]1[N:7]2[C:8]3[C:13]([N:14]=[CH:15][C:6]2=[N:5][CH:4]=[C:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=3.Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.[Pd]>[O:1]=[C:2]1[N:7]2[C:8]3[C:13]([NH:14][CH2:15][C:6]2=[N:5][CH:4]=[C:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12354442Ethyl 1-oxo-1H-pyrimido[1,2-a]quinoxaline-2-carboxylate

Product 1

HCID 13175315HCID 13175315, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of ethyl 1-oxo-1H-pyrimido [1,2-a] quinoxaline-2-carboxylate [Hermecz et al., J. Chem. Soc. Perkin I, 789 (1977)] were dissolved in 400 ml of ethyl acetate and 1.0 ml of HCl was added thereto followed by 300 mg of 5% Pd-C. The mixture obtained was hydrogenated for 5 hours at room temperature and atmospheric pressure. On completion of the reaction, the solution was made alkaline with NaHCO3 solution addition and filtered over celite. The organic phase was dried over MgSO4 and evaporated to dryness under nitrogen at 35° C. to obtain 4.2 g (83% yield) of ethyl 5,6-dihydro-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2-carboxylate melting at≃170° C.

Workup

  1. customThe mixture obtained
  2. customOn completion of the reaction
  3. filtrationfiltered over celite
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated to dryness under nitrogen at 35° C.

Sources & evidence

ORD record
ord-6938683f1805406e8056cec972a00db9
Source dataset
uspto-grants-1984_09
Patent number
US04472401

Reaction notes

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