Diethyl Malonate → Ethyl 4-hydroxy-1-(isoprenyl)-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 716684Notes

Reaction equation

[CH:1]([N:6]1[C:12](=[O:13])[O:11][C:9](=O)[C:8]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:7]12)=[CH:2][C:3](=[CH2:5])[CH3:4].[H-].[Na+].C(OCC)(=O)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[OH:11][C:9]1[C:8]2[C:7](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]([CH:1]=[CH:2][C:3](=[CH2:5])[CH3:4])[C:12](=[O:13])[C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

Reactant 3

HCID 7761Diethyl Malonate

HCID 24758Sodium hydride

HCID 131734149N-isoprenyl isatoic anhydride

Product 1

HCID 131734150Ethyl 4-hydroxy-1-(isoprenyl)-2-oxo-1,2-dihydroquinoline-3-carboxylate

Procedure

Reagents: Comp 18 (1.3 mmols, 0.3 g); Sodium hydride (1.3 mmols, 0.065 g); Diethyl malonate (6.5 mmols, 1.0 g). Yield: 0.08 g (21%), white solid, m.p.=123° C.-124° C.

Sources & evidence

ORD record: ord-7989c77f1bc140f9b058d13041caa0ab
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193688B2

Reaction notes

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