| Identification | Back Directory | [Name]
Methyl 2-amino-4-benzyloxy-5-methoxybenzoate | [CAS]
61032-42-6 | [Synonyms]
Methyl 2-amino-4-benzyloxy-5-methoxybenzoate
methyl 2-amino-5-methoxy-4-phenylmethoxybenzoate
2-Amino-4-benzyloxy-5-methoxybenzoic acid methyl ester
Benzoic acid, 2-amino-5-methoxy-4-(phenylmethoxy)-, methyl ester | [Molecular Formula]
C16H17NO4 | [MDL Number]
MFCD16620533 | [MOL File]
61032-42-6.mol | [Molecular Weight]
287.31 |
| Chemical Properties | Back Directory | [Melting point ]
131-132℃ | [Boiling point ]
450.0±40.0 °C(Predicted) | [density ]
1.205 | [storage temp. ]
2-8°C(protect from light) | [pka]
2.67±0.10(Predicted) | [Appearance]
Off-white to gray Solid |
| Hazard Information | Back Directory | [Uses]
Methyl 2-Amino-4-benzyloxy-5-methoxybenzoate can be used as reactant/reagent in preparation of cyanoquinolines as protein tyrosine kinase inhibitors. | [Synthesis]
Example 6 (Synthesis of methyl 2-amino-4-benzyloxy-5-methoxybenzoate): In a glass reactor equipped with a stirrer, a thermometer, a reflux condenser tube, and a hydrogen balloon, 4.0 g (12.6 mmol) of methyl 4-benzyloxy-5-methoxy-2-nitrobenzoate, 0.2 g of a 3 wt% platinum/carbon catalyst (60% moisture content, manufactured by NE CHEMCAT CORPORATION) and 20 mL of dimethoxyethane. The reaction was stirred at room temperature for 7 hours under hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was allowed to stand for 10 days, followed by filtration. The filtrate was concentrated under reduced pressure to give 3.17 g methyl 2-amino-4-benzyloxy-5-methoxybenzoate as a light brown solid (isolated yield: 87%). The physical property data of the product were as follows: 1H-NMR (CDCl3, δ/ppm): 3.81 (3H, s), 3.83 (3H, s), 5.09 (2H, s), 5.37 (2H, br s), 6.15 (1H, s), 7.31-7.41 (6H, m); CI-MS (m/e): 287 (M+). | [References]
[1] Patent: CN105541736, 2016, A. Location in patent: Paragraph 0044; 0047
[2] Organic Letters, 1999, vol. 1, # 11, p. 1835 - 1837
[3] Chemical Communications, 2016, vol. 52, # 87, p. 12869 - 12872
[4] Patent: EP2123627, 2009, A1. Location in patent: Page/Page column 6-7
[5] Patent: US2009/76044, 2009, A1. Location in patent: Page/Page column 26-27 |
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