Diethyl Malonate → Ethyl 2-oxo-1,2-dihydro-1,7-naphthyridine-3-carboxylate

HRID 1017711Notes

Reaction equation

HRID 1017711 reaction equation
C(O[C:6](=[O:16])[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[CH:14]=O)(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]=[N:10][CH:9]=2)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 14177126Tert-butyl 4-formylpyridin-3-ylcarbamate

Product 1

HCID 12204015Ethyl 2-oxo-1,2-dihydro-1,7-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 6-2 (2.20 g, 9.90 mmol, 1 equiv), diethyl malonate (3.00 mL, 19.8 mmol, 2.00 equiv), and piperidine (0.490 mL, 4.95 mmol, 0.500 equiv) in ethanol (50 mL) was heated at reflux for 20 h. The reaction mixture was allowed to cool to 23° C., then concentrated to about half its volume. The white crystals which formed were filtered and washed with cold ethanol (20 mL) to give 2-oxo-1,2-dihydro-[1,7]naphthyridine-3-carboxylic acid ethyl ester (6-3). 1H NMR (400 MHz, CDCl3) δ 12.15 (br s, 1H), 8.94 (s, 1H), 8.52 (d, 1H, J=5.2 Hz), 8.46 (s, 1H), 7.52 (d, 1H, J=5.2 Hz), 4.48 (q, 2H, J=7.1 Hz), 1.46 (t, 3H, J=7.1 Hz); TLC (EtOAc), Rf=0.13.

Workup

  1. temperatureat reflux for 20 h
  2. concentrationconcentrated to about half its volume
  3. customThe white crystals which formed
  4. filtrationwere filtered
  5. washwashed with cold ethanol (20 mL)

Sources & evidence

ORD record
ord-acf49ef85c1a47dabda48f2ec1a37206
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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