2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile Chemical Properties

Melting point:

127℃

Boiling point:

522.3±50.0 °C(Predicted)

Density 

1.29

storage temp. 

Sealed in dry,Room Temperature

pka

6.96±0.10(Predicted)

form 

Solid

color 

Light yellow to yellow

InChI

InChI=1S/C15H19N3O5/c1-21-14-10-13(18(19)20)12(11-16)9-15(14)23-6-2-3-17-4-7-22-8-5-17/h9-10H,2-8H2,1H3

InChIKey

FYCDMKYKGPHRFW-UHFFFAOYSA-N

SMILES

C(#N)C1=CC(OCCCN2CCOCC2)=C(OC)C=C1[N+]([O-])=O

Safety Information

HS Code 

2934999090

2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile Usage And Synthesis

Uses

4-Methoxy-5-[3-(morpholin-4-yl)propoxy]-2-nitrobenzonitrile is a useful research chemical compound used in the preparation of carbon-11 iressa as PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase.

Synthesis

General procedure for the synthesis of 4-methoxy-5-(3-morpholinopropoxy)-2-nitrobenzonitrile from 4-methoxy-3-(3-morpholinopropoxy)benzonitrile: In a 250 mL single-necked flask, 13.0 g (47.0 mmol) of 4-methoxy-3-(3-morpholinopropoxy)benzonitrile and 17 mL of concentrated nitric acid (65%, 376 mmol) were added followed by 17 mL of glacial acetic acid was added. The mixture was stirred at room temperature for about 2 hours until a large amount of solid precipitated, and stirring was continued for 1 hour. Upon completion of the reaction, 52 g of ice water was added to the reaction mixture and stirring was continued for 30 minutes. The solid product was collected by diafiltration and the filter cake was washed with ice water to a pH of about 7. After drying, 14.4 g of white solid product was obtained in 95.3% yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4102 - 4106
[2] Patent: CN107586279, 2018, A. Location in patent: Paragraph 0008; 0017
[3] Patent: CN105503749, 2016, A. Location in patent: Paragraph 0051; 0052
[4] Molecules, 2017, vol. 22, # 10,
[5] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48

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