Water → Methyl 4-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoate

HRID 487400Notes

Reaction equation

HRID 487400 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:17])[NH:10]2)[CH3:4].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:17])[N:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 200942525,7-diethyl-[1,6]naphthyridin-2(1H)-one

Product 1

HCID 19093769Methyl 4-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoateYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% dispersion in oil; 1.05 g) was added to a stirred solution of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (4.0 g) in DMF (75 ml) and the mixture was stirred until effervesence ceased. Methyl 4-bromomethylbenzoate (4.58 g) was added and the mixture was stirred under argon for 4 hours. The mixture was then poured into water and extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried (MgSO4) and solvent was removed by evaporation. The resultant solid was purified by flash chromatography, eluting with ethyl acetate/petroleum ether (3:1 v/v gradually increasing to 1:0 v/v) to give methyl 4-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoate as a solid (5.0 g); m.p. 128°-130° C.; NMR (d6 -DMSO): 1.15(t, 3H), 1.25(t, 3H), 2.69(q, 2H), 3.06(q, 2H), 3.83(s, 3H), 5.56(s, 2 H), 6.71(d, 1H), 7.04(s, 1H), 7.35(d, 2H), 7.91(d, 2H), 8.22(d, 1H); mass spectrum (+ve FAB, methanol/DMSO/NBA): 351 (M+H)+ ; microanalysis, found: C, 71.8; H, 6.3; N, 8.2%; C21H22N2O3 requires: C, 72.0; H, 6.3; N, 8.0%.

Workup

  1. stirringthe mixture was stirred under argon for 4 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with saturated sodium chloride solution
  4. dry with materialdried (MgSO4) and solvent
  5. customwas removed by evaporation
  6. customThe resultant solid was purified by flash chromatography
  7. washeluting with ethyl acetate/petroleum ether (3:1 v/v
  8. temperaturegradually increasing to 1:0 v/v)

Sources & evidence

ORD record
ord-92a8b962591b4ccc9d82727525b15204
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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