6-HYDROXYNICOTINIC ACID ETHYL ESTER Chemical Properties

Melting point:

150 °C

Boiling point:

347.5±42.0 °C(Predicted)

Density 

1.214±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

10.10±0.10(Predicted)

Appearance

Light brown to gray Solid

InChI

InChI=1S/C8H9NO3/c1-2-12-8(11)6-3-4-7(10)9-5-6/h3-5H,2H2,1H3,(H,9,10)

InChIKey

YYNSXKLGLKOLQZ-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

6-HYDROXYNICOTINIC ACID ETHYL ESTER Usage And Synthesis

Synthesis Reference(s)

Synthesis, p. 286, 1974 DOI: 10.1055/s-1974-23295

Synthesis

Preparation of ethyl 6-hydroxynicotinate: to a solution of 6-hydroxynicotinate (5.0 g, 35.9 mmol) in anhydrous ethanol (180 mL) was slowly added concentrated sulfuric acid (1.0 mL). The reaction mixture was stirred at 60 °C for 20 min, followed by the addition of additional ethanol (33.0 mL), and the reaction system was heated to reflux with continuous stirring for 6.5 h. The reaction mixture was then stirred for 6.5 h at 60 °C for 1.5 min. Upon completion of the reaction, the reaction solution was cooled to 0 °C and saturated aqueous sodium bicarbonate solution was slowly added to neutralize the reaction solution. Subsequently, the ethanol was removed by concentration under reduced pressure by rotary evaporator. The aqueous phase was extracted with ethyl acetate and the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give the white crystalline product ethyl 6-hydroxynicotinate (5.33 g, 89% yield). The product was characterized by 1H-NMR (CDCl3): δ 1.36 (3H, t, J = 7.1 Hz), 4.33 (2H, q, J = 7.1 Hz), 6.58 (1H, d, J = 9.5 Hz), 8.01 (1H, dd, J = 2.4, 9.5 Hz), 8.19 (1H, d, J = 2.4 Hz), 12.43 (1H brs).

References

[1] Patent: US2010/48610, 2010, A1. Location in patent: Page/Page column 83
[2] Journal of Fluorine Chemistry, 2017, vol. 203, p. 155 - 165
[3] Patent: EP1900735, 2008, A1. Location in patent: Page/Page column 14-15
[4] Journal of the Chemical Society, 1908, vol. 93, p. 1379

6-HYDROXYNICOTINIC ACID ETHYL ESTER(18617-50-0)Related Product Information

• METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE
• Ethyl 6-Hydroxyhexanoate
• 6-HYDROXYHEXANOIC ACID METHYL ESTER
• 4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER
• Ethyl nicotinate
• 2-Hydroxy-5-pyridinecarboxylic acid
• ISOPROPYL 5-CHLORO-1-(2,4-DICHLOROBENZYL)-6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE
• 5-Hydroxy-nicotinic acid ethyl ester ,97%
• DIETHYL 6-AMINO-2-OXO-1-[(3-PYRIDINYLCARBONYL)AMINO]-1,2-DIHYDRO-3,5-PYRIDINEDICARBOXYLATE
• ETHYL 1,2-DIAMINO-5-CYANO-4-(4-METHOXYPHENYL)-6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE
• ETHYL 7-CHLORO-2-METHYL-5-OXO-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXYLATE
• BENZYL 7-CHLORO-2-METHYL-5-OXO-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXYLATE
• DIETHYL 2-OXO-6-PIPERIDINO-1,2-DIHYDRO-3,5-PYRIDINEDICARBOXYLATE
• 2-ETHOXYETHYL 5-CHLORO-1-(2,4-DICHLOROBENZYL)-6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE
• 2-PROPYNYL 5-CHLORO-1-(2,4-DICHLOROBENZYL)-6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE
• ETHYL 5-OXO-2-[2-(3-PYRIDINYLAMINO)VINYL]-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXYLATE
• DIETHYL 6-ETHOXY-2-OXO-1,2-DIHYDRO-3,5-PYRIDINEDICARBOXYLATE
• DIETHYL 2-OXO-6-(1-PYRROLIDINYL)-1,2-DIHYDRO-3,5-PYRIDINEDICARBOXYLATE