68208-10-6

Basic information

• Product Name: 5-Ethoxy-2-oxazolecarboxylic Acid
• Synonyms: 5-Ethoxy-2-oxazolecarboxylic Acid;5-ETHOXYOXAZOLE-2-CARBOXYLIC ACID
• CAS NO: 68208-10-6
• Molecular Formula: C₆H₇NO₄
• Molecular Weight: 157.12408
• Product Categories: Heteorcycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 68208-10-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Ethoxy-2-oxazolecarboxylic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Ethoxy-2-oxazolecarboxylic Acid(68208-10-6)
• EPA Substance Registry System: 5-Ethoxy-2-oxazolecarboxylic Acid(68208-10-6)

Safety Data

• Hazardous Substances Data: 68208-10-6(Hazardous Substances Data)

Usage

Description

5-Ethoxy-2-oxazolecarboxylic Acid is an oxazole derivative, a heterocyclic compound characterized by the presence of an oxazole ring. It is known for its versatile chemical properties and is widely utilized in various synthetic applications.

Uses

Used in Organic Synthesis:
5-Ethoxy-2-oxazolecarboxylic Acid is used as a key intermediate in organic synthesis, particularly for the development of novel compounds with potential applications in various industries. Its unique structure allows for a range of chemical reactions, making it a valuable building block in the creation of new molecules.
Used in Pharmaceutical Industry:
5-Ethoxy-2-oxazolecarboxylic Acid is used as an intermediate in the synthesis of hydroxy-substituted aza-analogs of antitumor anthrapyrazoles. These compounds have shown potential as anticancer agents, targeting specific cancer cell pathways and exhibiting cytotoxic effects. The development of these aza-analogs aims to improve the efficacy and selectivity of current antitumor treatments, offering new therapeutic options for cancer patients.

Upstream product

• 68208-09-3 5-ethoxy-2-ethoxycarbonyloxazole 
• 29655-79-6 [(2-ethoxy-2-oxoethyl)amino]oxoacetic acid ethyl ester 

Downstream Products

• 15031-12-6 5-ethoxyoxazole 
• 19804-07-0 5-hydroxypyridine-3,4-dicarboxylic acid dimethyl ester 
• 174415-31-7 methyl 5-hydroxy-4-(2,5-difluorobenzoyl)nicotinate 
• 172779-17-8 methyl 5-hydroxy-4-(2'-fluoro-5'-chlorobenzoyl)nicotinate 

Relevant articles and documents

Synthesis of 4-hydroxy-6,9-difluorobenz[g]isoquinoline-5,10-diones and conversions to 4-hydroxy-6,9-bis[(aminoalkyl)amino]-benz[g]isoquinoline-5,10-diones

Synthetic procedures have been developed which lead to 4-hydroxy-6,9-difluorobenz[g]isoquinoline-5,10-dione (4a) and its 3-methyl analogue 4b. Attempts to displace the fluorides from 4a with N,N-dimethylethylenediamine were unsuccessful. Analogue 4a on treatment with N-(t-butoxycarbonyl)ethylene diamine led to 15, formed from addition of the nucleophilic amine to C-3. On the other hand, analogue 4b, on treatment with N,N-dimethylethylenediamine led to the anticipated difluoride displacement product 3c. The protection of the hydroxy group of 4a by benzylation with phenyldiazomethane led to 4c which on treatment with N-(t-butoxycarbonyl)ethylene diamine or N,N-dimethylethylenediamine led to the corresponding 6,9-bis-substituted analogues 18a and 18b, respectively. Reductive debenzylations of 18a and 18b by hydrogenation over Pearlman's catalyst also effected partial reductions of the quinone. However, air oxidation of the over reduced products led to 3a and 3b, respectively. Treatment of 3a with hydrogen chloride gas led to the hydrochloride salt of 3d. Addition of O-p-Methoxybenzyl-N,N'-diisopropylurea to 4a led to the p-methoxybenzyl analogue 4d. Treatment of 4d with N,N-dimethylethylene diamine or N-(t-butoxycarbonyl)ethylene diamine led to displacements of the fluorides to yield 18c and 18d, respectively. Deprotection of 18c to 3b was accomplished using methanesulfonic acid. Treatment of 18d with trifluoroacetic acid followed by addition of maleic acid led to dimaleate salt of 3d.