Diethyl Malonate → 3-Quinolinecarboxylic acid, 1,2-dihydro-4-hydroxy-1-(2-methylpropyl)-2-oxo-, ethyl ester

HRID 716685Notes

Reaction equation

HRID 716685 reaction equation
[CH2:1]([N:5]1[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:6]12)[CH:2]([CH3:4])[CH3:3].[H-].[Na+].C(OCC)(=O)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[OH:10][C:8]1[C:7]2[C:6](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[C:11](=[O:12])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 35786891-(2-methylpropyl)-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 693983113-Quinolinecarboxylic acid, 1,2-dihydro-4-hydroxy-1-(2-methylpropyl)-2-oxo-, ethyl ester

Procedure

Reagents: Comp 19 (1.36 mmols, 0.3 g); Sodium hydride (5.75 mmols, 0.138 g); Diethyl malonate (6.84 mmols, 1.1 g). Yield: 0.15 g (38%), yellow oil.

Sources & evidence

ORD record
ord-783626b20a934ebd9ee5eb5f87276e3d
Source dataset
uspto-grants-2015_11
Patent number
US09193688B2

Reaction notes

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