Water → 5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one

HRID 487398Notes

Reaction equation

HRID 487398 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].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19].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[CH2:25][C:24]1[CH:27]=[CH:28][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 200942525,7-diethyl-[1,6]naphthyridin-2(1H)-one

Product 1

HCID 189523915,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-oneYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% dispersion in oil; 0.2 g) was added to a stirred suspension of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (1.0 g) in DMF (10 ml) under an atmosphere of argon. The mixture was stirred until effervescence ceased and 4-nitrobenzyl bromide (1.1 g) was added. The mixture was then stirred for 16 hours. The mixture was then poured into water (50 ml) and extracted twice with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried (MgSO4) and solvent was removed by evaporation to give an oil. The oil was purified by flash chromatography, eluting with ethyl acetate/dichloromethane (1:4 v/v) to give 5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one (B) as a solid (1.03 g); m.p. 105°-106° C.; NMR (CDCl3): 1.22(t, 3H), 1.36(t, 3H), 2.77(q, 2H), 3.11(q, 2H), 5.57(s, 2H), 6.69(s, 1H), 6.77(d, 1H), 7.38(d, 2H), 8.03(d, 1H), 8.19(d, 2H); mass spectrum (CI, ammonia): 338 (M+H)+ ; microanalysis, found: C, 67.0; H, 5.7; N, 12.4%; C19H19N3O3 requires: C, 67.6; H, 5.7; N, 12.5%.

Workup

  1. stirringThe mixture was then stirred for 16 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with saturated sodium chloride solution
  4. dry with materialdried (MgSO4) and solvent
  5. customwas removed by evaporation
  6. customto give an oil
  7. customThe oil was purified by flash chromatography
  8. washeluting with ethyl acetate/dichloromethane (1:4 v/v)

Sources & evidence

ORD record
ord-adf980ad30cf4d4b8ef0cb57ee3ce6d8
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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