Diethyl Malonate → Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylate

HRID 1017708Notes

Reaction equation

HRID 1017708 reaction equation
C(O[C:6](=[O:16])[NH:7][C:8]1[C:13]([CH:14]=O)=[CH:12][CH:11]=[CH:10][N:9]=1)(C)(C)C.C(OCC)(=O)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].N1CCCCC1>C(O)C>[CH2:22]([O:21][C:19]([C:18]1[C:6](=[O:16])[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 14177125tert-butyl N-(3-formylpyridin-2-yl)carbamate

Product 1

HCID 11564777Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5-2 (1.53 g, 6.88 mmol, 1 equiv), diethyl malonate (2.09 mL, 13.8 mmol, 2.00 equiv), and piperidine (0.340 mL, 3.44 mmol, 0.500 equiv) in ethanol (20 mL) was heated at reflux for 16 h. The reaction mixture was allowed to cool to 23° C. The white crystals which formed were filtered and washed with ethanol (20 mL) to give 2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (5-3). 1H NMR (400 MHz, CDCl3) δ 11.9 (br s, 1H), 8.85 (dd, 1H, J=4.8, 1.7 Hz), 8.46 (s, 1H), 8.03 (dd, 1H, J=7.9, 1.6 Hz), 7.27 (dd, 1H, J=7.9, 4.8 Hz), 4.45 (q, 2H, J=7.1 Hz), 1.43 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureat reflux for 16 h
  2. customThe white crystals which formed
  3. filtrationwere filtered
  4. washwashed with ethanol (20 mL)

Sources & evidence

ORD record
ord-c29efdc3bff845f8a96e977caccd8402
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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