ETHYL 4-CHLORO-2-QUINAZOLINECARBOXYLATE Chemical Properties

Melting point:

100-101°C

Boiling point:

391.3±34.0 °C(Predicted)

Density 

1.341±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-0.74±0.30(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C11H9ClN2O2/c1-2-16-11(15)10-13-8-6-4-3-5-7(8)9(12)14-10/h3-6H,2H2,1H3

InChIKey

ZMAJSODACDWUAS-UHFFFAOYSA-N

SMILES

N1=C2C(C=CC=C2)=C(Cl)N=C1C(OCC)=O

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933599590

ETHYL 4-CHLORO-2-QUINAZOLINECARBOXYLATE Usage And Synthesis

Uses

Ethyl 4-Chloroquinazoline-2-carboxylate is a reactant used in the synthesis and evaluation of novel quinazoline-based anti-inflammatory agents acting as PDE4B inhibitors.

Synthesis

General procedure for the synthesis of ethyl 4-chloroquinazoline-2-carboxylate from ethyl 4-quinazolinone-2-carboxylate: To a suspension of ethyl 4-quinazolinone-2-carboxylate (1.2 g, 5.5 mmol) in chloroform (20 mL) was added sequentially N,N-dimethylformamide (6 drops) and thionyl chloride (4.8 mL, 66 mmol). The reaction mixture was heated to reflux for 4.5 hours. After completion of the reaction, it was cooled to room temperature and concentrated under reduced pressure to remove the solvent. Ice water was added to the residue and a white solid precipitated. The solid product was collected by filtration, washed with cold water and dried to afford ethyl 4-chloroquinazoline-2-carboxylate (1.26 g, 97% yield). The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.38 (dd, J = 0.74 Hz, 8.34 Hz, 1H), 8.31 (d, J = 8.48 Hz, 1H), 8.07 (m, 1H), 7.87 (m, 1H), 4.61 (q, J = 7.12 Hz, 2H), 1.50 (t, J = 7.14 Hz, 3H).IR spectra (diamond cell, cm-1 ) showed characteristic absorption peaks: νmax 1731.3, 1549.8, 1479.8, 1338.4, 1179.4, 913.0, 764.3, 693.9.Melting point is 86-88 °C.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 18, p. 5045 - 5048
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1701 - 1715
[3] Patent: WO2004/14844, 2004, A2. Location in patent: Page 187-188
[4] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 102 - 116

ETHYL 4-CHLORO-2-QUINAZOLINECARBOXYLATE(34632-69-4)Related Product Information

• 4-CHLORO-QUINAZOLINE
• ethyl 4-chloroquinazoline-6-carboxylate
• ETHYL 4-CHLORO-2-QUINAZOLINECARBOXYLATE
• 4-chloro-2-methylquinazoline
• 5-CHLOROPYRIMIDINE-2-CARBALDEHYDE
• ETHYL 4-CHLORO-6-METHOXYQUINAZOLINE-2-CARBOXYLATE
• 4-chloropyrimidine-2-carboxylic acid
• ETHYL 4,6-DICHLOROQUINAZOLINE-2-CARBOXYLATE