| Identification | Back Directory | [Name]
2-Amino-5-methoxybenzonitrile | [CAS]
23842-82-2 | [Synonyms]
6-Amino-m-anisonitrile
2-Cyano-4-methoxyaniline
5-Methoxyanthranilonitrile
2-Amino-5-methoxybenzonitrile
Benzonitrile,2-aMino-5-Methoxy- | [Molecular Formula]
C8H8N2O | [MDL Number]
MFCD05149280 | [MOL File]
23842-82-2.mol | [Molecular Weight]
148.162 |
| Chemical Properties | Back Directory | [Melting point ]
46-47℃ | [Boiling point ]
302℃ | [density ]
1.17 | [Fp ]
137℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Low-Melting Solid | [pka]
2.41±0.10(Predicted) | [color ]
Pale Yellow to Dark Beige |
| Hazard Information | Back Directory | [Synthesis]
Step 2: 2-nitro-5-methoxybenzonitrile (6.5 g, 36 mmol) obtained from Step 1 was dissolved in a 4:1 EtOAc:MeOH solvent mixture (150 mL) in a pressure vessel. Degassing was carried out by bubbling N2 into the solution for 10 min. Subsequently, 10% Pd/C catalyst (300 mg) was added to the solution. The vessel was sealed and pressurized with H2 to 25 psi. the reaction was shaken at room temperature for 20 min. Upon completion of the reaction, the vessel was purged with N2. The reaction mixture was filtered through diatomaceous earth and concentrated. The crude product was purified by fast column chromatography (SiO2 as stationary phase, gradient elution, eluent ratio 100:0 to 60:40 hexane:EtOAc) to afford 2-amino-5-methoxybenzonitrile (6.4 g, 100% yield) as a light yellow solid. | [References]
[1] Patent: WO2009/5646, 2009, A2. Location in patent: Page/Page column 186
[2] Tetrahedron Letters, 1984, vol. 25, # 8, p. 839 - 842
[3] Organic Preparations and Procedures International, 2009, vol. 41, # 5, p. 423 - 427
[4] Chemistry - A European Journal, 2004, vol. 10, # 10, p. 2487 - 2506
[5] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629 |
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