| Identification | Back Directory | [Name]
Benzonitrile, 5-amino-2-methoxy- (9CI) | [CAS]
214623-57-1 | [Synonyms]
Albb-004948
3-Cyano-4-methoxyaniline
2-Methoxy-5-amnobenzonitrile
5-amino-2-methoxybenzonitrile
2-Methoxy-5-aMinobenzonitrile
Benzonitrile, 5-amino-2-methoxy-
5-Amino-2-methoxybenzonitrile 98%
Benzonitrile, 5-amino-2-methoxy- (9CI)
5-amino-2-methoxybenzonitrile(SALTDATA: FREE) | [Molecular Formula]
C8H8N2O | [MDL Number]
MFCD00723841 | [MOL File]
214623-57-1.mol | [Molecular Weight]
148.16 |
| Chemical Properties | Back Directory | [Melting point ]
100 °C | [Boiling point ]
347.5±22.0 °C(Predicted) | [density ]
1.17±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Solid | [pka]
3.39±0.10(Predicted) | [Appearance]
Brown to gray Solid | [InChI]
InChI=1S/C8H8N2O/c1-11-8-3-2-7(10)4-6(8)5-9/h2-4H,10H2,1H3 | [InChIKey]
BZNMIDYUSWEPOM-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC(N)=CC=C1OC |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 5-amino-2-methoxybenzonitrile from 2-methoxy-5-nitrobenzonitrile: 2-methoxy-5-nitrobenzonitrile (1 equiv., 220 mg, 1.23 mmol), methanol (20 mL), and carbon-carrying palladium (10% mass, 10 mg) were added sequentially to a 100 mL round-bottom flask. The flask was connected to a three-way system and the reaction was stirred at room temperature. Evacuation was carried out and then filled with nitrogen, and this cycle was repeated three times, each time the nitrogen was filled for not less than 5 minutes. The reaction was allowed to proceed at room temperature for 30 minutes under hydrogen protection. Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration, the filtrate was concentrated and purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to afford 150 mg of the target product 5-amino-2-methoxybenzonitrile (Compound 7) as a white crystalline solid in 82% yield. | [References]
[1] Patent: CN106892871, 2017, A. Location in patent: Paragraph 0109; 0112; 0113
[2] Patent: CN105294584, 2016, A. Location in patent: Paragraph 0018; 0019
[3] Journal of the Chemical Society, 1945, p. 861,864
[4] Chemical Biology and Drug Design, 2018, vol. 91, # 2, p. 526 - 533 |
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