2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → Ethyl 4-hydroxy-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1241534Notes

Reaction equation

HRID 1241534 reaction equation
[NH2:1]/[C:2](/[CH3:9])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].ClC1C=C(Cl)C=C(Cl)C=1[C:19](C1C(Cl)=CC(Cl)=CC=1Cl)([C:23]([O-])=[O:24])[C:20]([O-])=[O:21]>COCCOCCOC>[OH:24][C:23]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([CH3:9])[NH:1][C:20](=[O:21])[CH:19]=1

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 21935290Di-(2,4,6-trichlorophenyl)malonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of ethyl 3-aminocrotonate (12.6 g, 97.5 mmol) and of intermediate 11 in diglyme (400 ml) was heated at 100° C. for 3 hours during which the product separated out. After cooling, diethylether (1.5 l) was added and the desired intermediate 12 was filtered (14.2 g, 75%). m.p. 243–245° C.

Workup

  1. customseparated out
  2. temperatureAfter cooling
  3. additiondiethylether (1.5 l) was added
  4. filtrationthe desired intermediate 12 was filtered (14.2 g, 75%)

Sources & evidence

ORD record
ord-fade81a4391d49c7b2349a65d41aa9d0
Source dataset
uspto-grants-2006_10
Patent number
US07115608B2

Reaction notes

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