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

HRID 1587519Notes

Reaction equation

HRID 1587519 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 effervescence 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, 2H), 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-81f0c9a0d60944048202bdc25bfa28c4
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

Loading…