2-Chloroethyl acetoacetate → HCID 14304814, compound

HRID 231816Notes

Reaction equation

HRID 231816 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:11]([O:17][CH2:18][CH2:19][Cl:20])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25]>C(O)(C)C>[CH3:27][O:26][C:24]([C:23]1[CH:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[N:8]=2)[C:12]([C:11]([O:17][CH2:18][CH2:19][Cl:20])=[O:16])=[C:13]([CH3:15])[NH:21][C:22]=1[CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 1086052-Chloroethyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 27483386-Formylpicolinonitrile

Product 1

HCID 14304814HCID 14304814, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6-Cyano-2-pyridine aldehyde (1.613 g, 12.2 mmol), chloroethyl acetoacetate (2.009 g, 12.2 mmol) and methyl 3-aminocrotonate (1.364 g, 12.2 mmol) were dissolved in 16 ml of isopropanol, and the solution was stirred at 35° to 40° C. under a nitrogen gas stream for 14 hours. The reaction solvent was distilled off under reduced pressure, and the residue was purified by column chromatography [silica gel; ethyl acetate-n-hexane (5:6)]. The crude product thus obtained was recrystallized from isopropyl ether-methanol to obtain 1.546 g (34% yield) of the above-captioned compound.

Workup

  1. distillationThe reaction solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography [silica gel; ethyl acetate-n-hexane (5:6)]
  3. customThe crude product thus obtained
  4. customwas recrystallized from isopropyl ether-methanol

Sources & evidence

ORD record
ord-86e87c7687034558a4452c59ae2c93af
Source dataset
uspto-grants-1989_07
Patent number
US04849429

Reaction notes

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