Urea → 4-Oxo-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

HRID 59952

Reaction equation

HRID 59952 reaction equation
[O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH:13](OCC)(OCC)OCC.N[C:24]([NH2:26])=O>C1(C)C(C)=CC=CC=1>[O:1]=[C:2]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:24][NH:26][CH:13]=[C:3]1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 1176UreaHCID 31214Ethyl orthoformateHCID 74591Dimethyl 3-oxoglutarate

Product 1

HCID 113901994-Oxo-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl esterYield 82.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of dimethyl 3-oxopentanedioate (12 g, 69 mmol), CH(OEt)3 (15.1 g, 100 mmol) and urea (6 g, 100 mmol) in xylene (25 mL) was heated to reflux for 3 hours. The mixture was cooled to room temperature and the precipitate was filtered, washed with xylene and DCM to afford the title compound as white solid (yield 82.3%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe precipitate was filtered
  4. washwashed with xylene and DCM

Sources & evidence

ORD record
ord-b7e52f2fac1f4af8908e41e0da758d72
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Linked notes

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