Allyl iodide → 7-Methoxy-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

HRID 656878Notes

Reaction equation

HRID 656878 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[N:5][CH:4]=1.[H-].[Na+].[CH2:16](I)[CH:17]=[CH2:18]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[N:10]2[CH2:18][CH:17]=[CH2:16])=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 578154107-Methoxy-1,5-naphthyridin-2(1H)-one

Product 1

HCID 585793327-Methoxy-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-oneYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7-(Methoxy)-1,5-naphthyridin-2(1H)-one (5.958 g, 33.852 mmol) was suspended in dry DMF (100 ml) under argon at rt, and the stirred suspension was treated with sodium hydride (2.98 g, 60% suspension in oil, 74.48 mmol) and stirred at rt for 0.5 h. Allyl iodide (6.88 ml, 74.475 mmol) was then added. The reaction was stirred at rt for 0.5 h and then the mixture was diluted with water to 300 ml and extracted with DCM (3×300 ml). The DCM extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give a brown gum which was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient to provide the desired compound (4.096 g, 56%). Mixed fractions could be triturated with diethyl ether to provide further compound (0.95 g, 13%).

Workup

  1. stirringThe reaction was stirred at rt for 0.5 h
  2. extractionextracted with DCM (3×300 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a brown gum which
  7. customwas purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient

Sources & evidence

ORD record
ord-ba163f2b084b497aa79e3b41b2a1e947
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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