Triethylamine → HCID 69563164, compound

HRID 1840410Notes

Reaction equation

HRID 1840410 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 dichloromethane-methanol (15:1). The desired compound was obtained as a dark red oil which contained 1 equivalent of triethylamine. ESI−MS: m/z 234 (MH+); 1H-NMR (CDCl3): δ1.26-1.38 (15H, m), 2.63 (3H, s), 3.28 (6H, q, J=3.3 Hz), 4.22 (2H, q, J=4.2 Hz), 7.29 (1H, s), 8.58 (1H, s).

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-6c0524d6e08c4ce0b11474568eeb2295
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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