Ethanol → Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate

HRID 487389Notes

Reaction equation

HRID 487389 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=[O:13].C([C:16](CC)([C:20]([O-:22])=O)[C:17]([O-:19])=[O:18])C.[CH2:25](O)[CH3:26]>N1CCCCC1>[CH2:10]([C:4]1[N:5]=[C:6]([CH2:8][CH3:9])[CH:7]=[C:2]2[C:3]=1[C:12]([OH:13])=[C:16]([C:17]([O:19][CH2:25][CH3:26])=[O:18])[C:20](=[O:22])[NH:1]2)[CH3:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 69515632,2-DiethylpropanedioateHCID 190937814-Amino-2,6-diethyl-pyridine-3-carbaldehyde

Product 1

HCID 54684680Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

4-amino-2,6-diethylpyridine-3-carbaldehyde (1.78 g), diethylmalonate (1.92 g), ethanol (15 ml) and piperidine (4 drops) were heated at reflux for 16 hours. Volatile material was removed by evaporation and the residue was recrystallised from ethyl acetate/petroleum ether to give ethyl 5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate (B) (1.4 g), m.p. 159°-160° C.; NMR (CDCl3): 1.34(t, 3H), 1.38(t, 3H), 1.47(t, 3H), 2.87(q, 2H), 3.14(q, 2H), 4.47(q, 2H), 7.03(s, 1H), 8.78(s, 1H), 12.2(s, 1H); mass spectrum (CI, ammonia): 275 (M+H)+ ; microanalysis, found: C, 65.8; H, 6.8; N, 10.4%; C15H18N2O3 requires: C, 65.7; H, 6.6; N, 10.2%.

Workup

  1. temperatureat reflux for 16 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-9c17c46f14f949cd908330fb5aa817d4
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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