Diethyl Oxalate → Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

HRID 2093104

Reaction equation

HRID 2093104 reaction equation
[O-]CC.[Na+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>C1(C)C=CC=CC=1>[N+:22]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:16]=1[CH2:15][C:6](=[O:8])[C:5]([O:12][CH2:13][CH3:14])=[O:11])([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 2723922Sodium ethoxide

Product 1

HCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of freshly prepared sodium ethoxide was added diethyl oxalate (1.5 eq.) followed by 4-methyl-3-nitro pyridine (1 eq.) in toluene and reaction mixture was stirred overnight. It was then concentrated under reduced pressure and acidified with acetic acid to obtained red solid, which on further purification, by column chromatography provided the ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. customto obtained red solid, which
  3. customon further purification

Sources & evidence

ORD record
ord-833d403d014e41518e19f7df95ba7f70
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Linked notes

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