(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one Chemical Properties

Melting point:

113℃

Boiling point:

281℃

Density 

1.070

Flash point:

124℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.74±0.70(Predicted)

color 

Dark Brown to Very Dark Brown

InChI

InChI=1S/C10H12N2O/c1-12(2)7-5-10(13)9-4-3-6-11-8-9/h3-8H,1-2H3/b7-5+

InChIKey

MZLRFUCMBQWLNV-FNORWQNLSA-N

SMILES

C(C1=CC=CN=C1)(=O)/C=C/N(C)C

(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one Usage And Synthesis

Description

(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is a pharmaceutical intermediate used as an intermediate of nilotinib, a targeted anticancer drug for the treatment of chronic myeloid leukaemia (CML).

Uses

(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one acts as a reagent for the synthesis of oxindole-linked indolyl-pyrimidine derivatives which are potential cytotoxic agents.

Synthesis

Example-2: Preparation of 3-dimethylamino-1-pyridin-3-ylacrylone Method A: 3-Acetylpyridine (25 g, 0.20 mol), N,N-dimethylformamide dimethyl acetal (37 g, 0.31 mol) and acetic acid (2.5 ml) were mixed and the reaction was heated at 90-95°C for 2 hours, during which time the methanol produced was continuously removed. After completion of the reaction, excess methanol in the reaction was removed by distillation under reduced pressure. The reaction mixture was diluted with water and extracted with dichloromethane (125 ml). The organic layer was washed with water and the solvent was removed by distillation under reduced pressure to afford 34 g (92% yield) of (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one with a purity of 99.1% by HPLC analysis.

Solubility in organics

(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is soluble in chloroform and dichloromethane.

References

[1] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[2] RSC Advances, 2018, vol. 8, # 47, p. 26828 - 26836
[3] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[4] Patent: WO2011/39782, 2011, A1. Location in patent: Page/Page column 14
[5] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495

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