Ethyl 4,5-Bis(2-methoxyethoxy)-2-nitrobenzoate

• CAT Number: R025077
• CAS Number: 179688-26-7
• Molecular Formula: C15H21NO8
• Molecular Weight: 343.332
• Purity: ≥95%
• Synonyms: 4,​5-Bis(2-​methoxyethoxy)​-​2-​nitro-​benzoic Acid Ethyl Ester
• Storage: 3 years -20C powder
• IUPAC Name: ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate
• InChI: InChI=1S/C15H21NO8/c1-4-22-15(17)11-9-13(23-7-5-20-2)14(24-8-6-21-3)10-12(11)16(18)19/h9-10H,4-8H2,1-3H3
• InChIKey: VOHOFZNVWZWVMA-UHFFFAOYSA-N
• SMILES: CCOC(=O)C1=CC(=C(C=C1[N+](=O)[O-])OCCOC)OCCOC

Ethyl 4,5-Bis(2-methoxyethoxy)-2-nitrobenzoate (CAS 179688-26-7)  is used in the syntheses of 4-(indol-3-yl)quinazolines as epidermal growth factor receptor tyrosine kinase inhibitors. It is also used to prepare Erlotinib hydrochloride, a useful drug in treatment of non-​small-​cell lung cancer.

Reference

1.Lüth, Anja, and Werner Löwe. "Syntheses of 4-(indole-3-yl) quinazolines–A new class of epidermal growth factor receptor tyrosine kinase inhibitors." European journal of medicinal chemistry 43.7 (2008): 1478-1488.

2.Adv Pharm Bull. 2012;2(1):119-22. doi: 10.5681/apb.2012.017. Epub 2012 May 5.Modified synthesis of erlotinib hydrochloride.Barghi L(1), Aghanejad A, Valizadeh H, Barar J, Asgari D.

 

PURPOSE: An improved and economical method has been described for the synthesis of erlotinib hydrochloride, as a useful drug in treatment of non-small-cell lung cancer.

 

METHOD: Erlotinib hydrochloride was synthesized in seven steps starting from 3, 4-dihydroxy benzoic acid. In this study, we were able to modify one of the key steps which involved the reduction of the 6-nitrobenzoic acid derivative to 6-aminobenzoic acid derivative. An inexpensive reagent such as ammonium formate was used as an in situ hydrogen donor in the presence of palladium/charcoal (Pd/C) instead of hydrogen gas at high pressure.

 

RESULT: This proposed method proceeded with 92% yield at room temperature. Synthesis of erlotinib was completed in 7 steps with overall yield of 44%.

 

CONCLUSION: From the results obtained it can be concluded that the modified method eliminated the potential danger associated with the use of hydrogen gas in the presence of flammable catalysts. It should be mentioned that the catalyst was recovered after the reaction and could be used again.