4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER Chemical Properties

Melting point:

214-217°

Boiling point:

339.4±42.0 °C(Predicted)

Density 

1.380

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

4.50±1.00(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C8H9NO4/c1-2-13-8(12)5-4-9-7(11)3-6(5)10/h3-4H,2H2,1H3,(H2,9,10,11)

InChIKey

QDHHLXABEXNRJX-UHFFFAOYSA-N

SMILES

C1NC(=O)C=C(O)C=1C(OCC)=O

CAS DataBase Reference

6975-44-6

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29339900

4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER Usage And Synthesis

Chemical Properties

White solid

Uses

Ethyl 4,?6-?dihydroxynicotinate has been used as a reactant is the synthesis of pyridazinopyrimidinone and pyridopyrimidinone derivatives as PDE5 inhibitors and for the synthesis of pyridone diaryl ether non-nucleoside inhibitors of HIV-1 reverse transcriptase.

Synthesis

The general procedure for the synthesis of ethyl 4,6-dihydroxynicotinate from ethanoic anhydride and diethyl 1,3-acetone dicarboxylate was as follows: diethyl 3-oxoglutarate (101 g, 0.5 mol), triethyl orthoformate (81.4 g, 0.55 mol), and acetic anhydride (102 g, 1 mol) were mixed and the reaction was maintained at a temperature of 120 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and dissolved in dichloromethane (1 L). Subsequently, the solution was cooled to 0 °C, 30% ammonia (80 mL) was slowly added, and then the reaction mixture was gradually warmed to room temperature and left overnight. The reaction mixture was extracted twice with water and the aqueous phase was adjusted to pH 5 with concentrated hydrochloric acid. after acidification, the precipitate was collected by filtration to afford ethyl 4,6-dihydroxynicotinate (60.0 g, 60% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.99 (s, 1H), 5.58 (s, 1H), 4.23 (q, J = 6.8, 14.0 Hz, 2H), 1.25 (t, J = 7.2 Hz, 3H); MS (ESI) m/z: 184.1 [M + H]+.

References

[1] Patent: US8461179, 2013, B1. Location in patent: Page/Page column 66

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