| Identification | Back Directory | [Name]
4-HYDROXY-6-METHOXYQUINOLINE | [CAS]
23432-39-5 | [Synonyms]
Nsc76096
6-METHOXYQUINOLIN-4-OL
6-METHOXY-4-QUINOLINOL
6-Methoxyl-4-quinolinol
6-Methoxyquinoline-4-ol
4-Quinolinol, 6-methoxy-
6-METHOXYQUINOLIN-4(1H)-ONE
6-METHOXY-4(1H)-QUINOLINONE
6-METHOXY-4-HYDROXYQUINOLINE
4-HYDROXY-6-METHOXYQUINOLINE
6-Methoxyquinoline-4(1H)-one
6-Methxoyl-4(1H)-quinolinone
4-Hydroxyl-6-methoxyquinoline
6-Methoxy-4(1H)-quinolinone([13788-72-2]) | [EINECS(EC#)]
803-465-5 | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD00014662 | [MOL File]
23432-39-5.mol | [Molecular Weight]
175.18 |
| Chemical Properties | Back Directory | [Melting point ]
225-244 °C(Solv: water (7732-18-5)) | [Boiling point ]
351.8±22.0 °C(Predicted) | [density ]
1.258±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
solid | [pka]
4.40±0.40(Predicted) | [Appearance]
Off-white to gray Solid | [InChI]
1S/C10H9NO2/c1-13-7-2-3-9-8(6-7)10(12)4-5-11-9/h2-6H,1H3,(H,11,12) | [InChIKey]
RVTLXJLNIDCHKT-UHFFFAOYSA-N | [SMILES]
COc1ccc2nccc(O)c2c1 |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 4-hydroxy-6-methoxyquinoline-3-carboxylic acid from 4-hydroxy-6-methoxyquinoline-3-carboxylic acid: 4-hydroxy-6-methoxyquinoline-3-carboxylic acid (7, 15.7 g, 72 mmol) was dissolved in 80 mL of diphenyl ether and heated to 245 °C in a metal bath for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and dissolved in 200 mL of hexane. The mixture was stirred for 3 hours and then filtered. The resulting solid was washed with ethyl acetate and dried to give 6-methoxyquinolin-4-ol (8, 12.5 g, 72 mmol, 100% yield). The product was characterized by 1H-NMR (DMSO-d6): δ= 3.81 (s, 3H), 5.99 (d, 1H), 7.28 (dd, 1H), 7.48-7.53 (m, 2H), 7.86 (d, 1H), 11.87 (bs, 1H).Results of the LC-MS analysis: retention time (Rt) = 0.87 min; mass spectrum (MS): m/z = 176 [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] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 5, p. 821 - 824 |
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