Diethyl Ether → Ethyl 4-hydroxy-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 251572Notes

Reaction equation

HRID 251572 reaction equation
ClC1C=C(Cl)C=C(Cl)C=1[O:10][C:11](=O)[CH2:12][C:13](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:14].[NH2:26]/[C:27](/[CH3:34])=[CH:28]\[C:29]([O:31][CH2:32][CH3:33])=[O:30].C(OCC)(=O)C.CCOCC>BrC1C=CC=CC=1>[CH2:32]([O:31][C:29]([C:28]1[C:13]([OH:14])=[CH:12][C:11](=[O:10])[NH:26][C:27]=1[CH3:34])=[O:30])[CH3:33]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 2783450Bis(2,4,6-trichlorophenyl) propanedioate

Product 1

HCID 54688208Ethyl 4-hydroxy-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 7961BromobenzeneSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of malonic acid bis(2,4,6-trichloro-phenyl)ester (13.3 g, 0.03 mol) and ethyl 3-aminocrotonate (3.87 g, 0.03 mol) in bromobenzene (25 mL) is heated at 155° C. for 30 minutes. The mixture is cooled to room temperature. Ethyl acetate (50 mL) and ether (50 mL) are added. The solid is collected and purified by filtration through a short silica gel column (25% ethyl acetate/ether) to give 4-hydroxy-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester. 1H NMR: (CDCl3) 5.85 (s, 1H), 4.38 (q, 2H), 2.68 (s, 3H), 1.39 (t, 3H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customThe solid is collected
  3. filtrationpurified by filtration through a short silica gel column (25% ethyl acetate/ether)

Sources & evidence

ORD record
ord-e5fead0b6c504524badd8a4a1df8277f
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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