Triethylamine → HCID 69563164, compound

HRID 496739Notes

Reaction equation

HRID 496739 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[C:4]([C:11]([OH:13])=O)[CH:3]=1.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15]C(C)=O.C(N(CC)CC)C>C(OC(=O)C)(=O)C>[CH2:21]([O:20][C:14]([CH:15]1[C:8](=[O:10])[C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][C:4]=2[C:11]1=[O:13])=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 21816769HCID 21816769, compound

Product 1

HCID 69563164HCID 69563164, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

6-Methyl-pyridine-3,4-dicarboxylic acid (440 mg) (see, Emil J. Moriconi and Francis A. Spano, J. Am. Chem. Soc., Vol. 86, pp. 38-46, 1964) was suspended in acetic anhydride (10 ml) and the mixture was refluxed for 10 minutes. Ethyl acetoacetate (0.325 ml) and triethylamine (0.745 ml) were dropwise added to the mixture at room temperature and the mixture was stirred overnight. The mixture was concentrated to dryness and purified by silica gel column chromatography developed by dichloromethane and by dichloro-methane-methanol (15:1). The desired compound was obtained as a dark red oil which contained 1 equivalent of triethylamine.

Workup

  1. temperaturethe mixture was refluxed for 10 minutes
  2. concentrationThe mixture was concentrated to dryness
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-ab1be21333a747df83ac0e49b4f719fb
Source dataset
uspto-grants-2005_09
Patent number
US06946472B2

Reaction notes

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