Diethyl Malonate → Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 901218Notes

Reaction equation

[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:12]([N:19]1[C:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:22](=O)[O:21]C1=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:24]2[C:23]([C:22]=1[OH:21])=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:4])[CH3:7]

Participants

Reactant 2

HCID 7761Diethyl Malonate

HCID 134251031-Benzyl-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione

Product 1

HCID 54729304Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Procedure

Diethyl malonate can then be reacted with the 1-benzyl-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione (2) to yield the intermediate 1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (3) as shown in Scheme 3:

Sources & evidence

ORD record: ord-09d9de3f43124adcb512c8b8b6f31305
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361760B2

Reaction notes

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