| Identification | More | [Name]
4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID | [CAS]
28027-16-9 | [Synonyms]
3-CARBOXY-4-HYDROXY-6-METHOXYQUINOLINE
4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID
AKOS BB-8879
BUTTPARK 20\09-62 | [Molecular Formula]
C11H9NO4 | [MDL Number]
MFCD00024003 | [Molecular Weight]
219.19 | [MOL File]
28027-16-9.mol |
| Chemical Properties | Back Directory | [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 | [InChI]
1S/C11H9NO4/c1-16-6-2-3-9-7(4-6)10(13)8(5-12-9)11(14)15/h2-5H,1H3,(H,12,13)(H,14,15) | [InChIKey]
YUXLPEGMXYHPCZ-UHFFFAOYSA-N | [SMILES]
O=C(O)C1=C(O)C2=C(C=CC(OC)=C2)N=C1 | [CAS DataBase Reference]
28027-16-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [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 |
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