| Identification | More | [Name]
4-Methoxy-1H-indole-2-carboxylic acid | [CAS]
103260-65-7 | [Synonyms]
4-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
4-METHOXY-2-INDOLECARBOXYLIC ACID
4-METHOXYINDOLE-2-CARBOXYLIC ACID
AKOS JY2082663
IFLAB-BB F2137-0008
4-Methoxyindole-2-CarboxylicAcid99% | [EINECS(EC#)]
607-884-2 | [Molecular Formula]
C10H9NO3 | [MDL Number]
MFCD02664458 | [Molecular Weight]
191.18 | [MOL File]
103260-65-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
234-235 °C | [Boiling point ]
447.6±25.0 °C(Predicted) | [density ]
1.381±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
solid | [pka]
4.52±0.30(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C10H9NO3/c1-14-9-4-2-3-7-6(9)5-8(11-7)10(12)13/h2-5,11H,1H3,(H,12,13) | [InChIKey]
ZZAVIQXQBBOHBB-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(OC)=CC=C2)C=C1C(O)=O | [CAS DataBase Reference]
103260-65-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
4-Methoxy-1H-indole-2-carboxylic acid can be used as a precursor to prepare 4-methoxy-1H-indole-2-carboxamide via treatment with thionyl chloride in dry tetrahydrofuran, followed by reaction with ammonia[6]. | [Synthesis]
Methyl 4-methoxy-2-indolecarboxylate (4 g, 19.49 mmol, 1 eq) was added to an aqueous solution of sodium hydroxide (2M, 98 mL, 0.20 mmol, 10 eq). The suspension was stirred and heated until the reaction mixture was uniform, and then the mixture was refluxed for 30 minutes with heating. The mixture solution was acidified, and the resulting precipitate was extracted three times with ethyl acetate (100 mL). The extracts were combined, washed with water, dried over magnesium sulfate, and concentrated to give a white solid of 4-methoxy-1H-indole-2-carboxylic acid (3.71 g, yield 99 per cent). | [References]
[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
[2] Patent: EP1533299, 2005, A1. Location in patent: Page/Page column 8
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 19, p. 3624 - 3634
[4] Patent: WO2008/60621, 2008, A2. Location in patent: Page/Page column 118
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 5, p. 483 - 486 |
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