4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

278-279 °C (decomp)

Boiling point:

418.6±45.0 °C(Predicted)

Density 

1.444±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

0.74±0.30(Predicted)

Appearance

Off-white to light yellow Solid

CAS DataBase Reference

28027-16-9(CAS DataBase Reference)

Safety Information

HS Code 

2933499090

4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-hydroxy-6-methoxyquinoline-3-carboxylic acid from ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate: ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate (17.8 g, 72 mmol) was suspended in 170 mL of aqueous 2 N sodium hydroxide solution, heated to 90 °C, and the reaction was maintained for 1.5 h. The mixture was cooled to room temperature and slowly poured into ice water. Upon completion of the reaction, the mixture was cooled to room temperature, slowly poured into ice water and the pH was adjusted to 5 with 2 N hydrochloric acid.The precipitated solid was collected by filtration, washed with cold water and dried to give 4-hydroxy-6-methoxyquinoline-3-carboxylic acid (15.8 g, 72 mmol, 99% yield). The product was characterized by 1H-NMR (DMSO-d6): δ= 3.91 (s, 3H), 7.53 (dd, 1H), 7.64 (d, 1H), 7.82 (d, 1H), 8.80 (d, 1H), 13.63 (bs, 1H), 15.55 (s, 1H).Results of LC-MS analysis: retention time (Rt) = 1.20 min; Mass spectrum (MS): m/z = 220 [M+H]+.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 8, p. 794 - 796
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1204,1206
[3] Organic Syntheses, 1955, vol. Coll. Vol. III, p. 272
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 1659,1660
[5] Journal of the Chemical Society, 1946, p. 1033,1035

4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID(28027-16-9)Related Product Information

• ETHYL 4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLATE
• Oxolinic acid
• 4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID
• Proquinolate
• Ciproquinate
• Quincarbate
• buquinolate
• Miloxacin
• 4-Hydroxy-5-methoxyquinoline- 3-carboxylic acid
• Methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate
• 4-HYDROXY-7-METHOXYQUINOLINE-3-CARBOXYLIC ACID
• 4-HYDROXY-7-METHOXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• 4-HYDROXY-8-METHOXYQUINOLINE-3-CARBOXYLIC ACID,4-Hydroxy-8-methoxyquinoline-3-carboxylic acid ,95%
• (S)-1-Boc-3-methylpiperazine
• 4-HYDROXY-8-METHOXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• 4-HYDROXY-6-METHOXYQUINOLINE
• 4-HYDROXY-6-METHOXYQUINOLINE
• 6-Methoxyquinoline