Diethyl Malonate → Ethyl (6-methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 2194538Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)=[CH:5][CH:4]=1.[C:18](OCC)(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].N1CCCCC1>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:10]3[C:11](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]2=[O:25])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6.4 g (28 mmol) of 2-(6-methoxy-3-pyridinylamino)nicotinaldehyde was dissolved in ethanol (50 mL), and 6.7 g (42 mmol) of diethyl malonate and 0.95 g (11 mmol) of piperidine were added thereto. The resulting mixture was stirred for 4 hours at 100° C. The solvent was distilled off under reduced pressure from the reaction mixture, and the residue was washed with a mixed solution of ethyl acetate and diisopropyl ether. Thus, 4.1 g of the title compound was obtained as a pale yellow solid (yield: 45%).

Workup

distillationThe solvent was distilled off under reduced pressure from the reaction mixture
washthe residue was washed with a mixed solution of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record: ord-fc6e3a2b56ae49ee837fb70aad3b551c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334236B2

Reaction notes

Loading…