Ethyl Acetate → Methyl 6-oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxylate

HRID 656921Notes

Reaction equation

HRID 656921 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][C:4]=2[NH:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:22](I)[CH:23]=[CH2:24].CCOC(C)=O>CN(C=O)C>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][C:4]=2[N:3]1[CH2:24][CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11166Allyl iodide2×HCID 11430Potassium CarbonateHCID 68818275Methyl 6-oxo-5,6-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 68816926Methyl 6-oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of methyl 6-oxo-5,6-dihydro-1,5-naphthyridine-3-carboxylate (1.963 g, 5.36 mmol) in DMF (32 ml) was treated with K2CO3 (2.95 g, 21.3 mmol), stirred for 10 mins and then treated with allyl iodide (0.535 ml, 5.88 mmol), heated for 7 h at 75° C., further allyl iodide (0.15 ml, 0.89 mmol) was added and the reaction heated for a further 2 h. The reaction was treated with EtOAc, washed with water three times. The combined aqueous phases were then re-extracted with EtOAc and this washed with water twice. The combined organic phases were dried, evaporated and the residue was subjected to column chromatography on silica gel using a 1:1 EtOAc:hexane gradient to provide the desired compound (0.809 g, 62%).

Workup

  1. temperaturethe reaction heated for a further 2 h
  2. washwashed with water three times
  3. extractionThe combined aqueous phases were then re-extracted with EtOAc
  4. washthis washed with water twice
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-77be01d598af4bca812a58b245c24612
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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