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

HRID 1492310Notes

Reaction equation

HRID 1492310 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 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% dispersion in oil; 0.2 g) was added to a stirred solution of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (1.0 g) in DMF (10 ml) under argon. The mixture was stirred for 15 minutes, then 4-nitrobenzyl bromide (1.1 g) was added and the mixture was stirred for 16 hours. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with saturated sodium chloride solution (10 ml), dried (MgSO4) and the solvent was removed by evaporation. The residue 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 yellow solid (1.4 g), m.p. 105°-106° C.; NMR (CDCl3): 1.22(t, 3H), 1.36(t, 3H), 2.77(q, 2H), 3.11(q, 2H), 5.77(s, 2H), 6.69(s, 1H), 6.77(d, 1H), 7.38(d, 2H), 8.03(d, 1H), 8.19(d, 2H); mass spectrum (+ve CI): 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 stirred for 16 hours
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. washThe combined extracts were washed with saturated sodium chloride solution (10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/dichloromethane (1:4 v/v)

Sources & evidence

ORD record
ord-c9e4f49abbcf474c997cd254fa39c3bd
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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