| Identification | Back Directory | [Name]
METHYL 2-AMINO-5-METHYLBENZOATE | [CAS]
18595-16-9 | [Synonyms]
NSC 3109
SunaroMe UVA
o-(Methoxycarbonyl)aniline
Methyl 5-methylanthranilate
METHYL 2-AMINO-5-METHYLBENZOATE
[2-(Methoxycarbonyl)phenyl]aMine
2-Amino-5-methylbenzoic acid methyl ester
5-Methyl-2-aMinobenzoic acid Methyl ester | [Molecular Formula]
C9H11NO2 | [MDL Number]
MFCD00661547 | [MOL File]
18595-16-9.mol | [Molecular Weight]
165.19 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [Melting point ]
54-56°C | [density ]
1.132 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Dichloromethane, Ethyl Acetate, Methanol | [form ]
Solid | [color ]
Yellow to Brown |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
A useful synthetic intermediate | [Synthesis]
Methyl 5-methyl-2-nitrobenzoate (8 g, 41.025 mmol) was used as a raw material in a solvent mixture of methanol (80 mL) and water (10 mL), and cooled to 0 °C. Subsequently, zinc powder (13.33 g, 205.128 mmol) and NH4Cl (17.6 g, 328.2 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 12 h. The reaction progress was monitored by TLC (unfolding agent: 20% ethyl acetate/hexane). After completion of the reaction, the mixture was filtered and the filtrate was evaporated to give the crude product. The crude product was alkalized with saturated NaHCO3 solution and extracted with dichloromethane (2 x 20 mL). The organic layers were combined, dried with Na2SO4, filtered and the solvent was evaporated to give the target compound methyl 2-amino-5-methylbenzoate (yield: 4 g, 60%).1H NMR (400 MHz, CDCl3) data were as follows: δ 7.65 (s, 1H), 7.25 (s, 1H), 7.10-7.07 (q, 1H, J=8Hz), 6.58 (d, 1H), 3.86 (s, 3H), 2.22 (s, 3H). | [References]
[1] Patent: WO2015/38417, 2015, A1. Location in patent: Paragraph 151; 152
[2] Journal of the Chemical Society, 1930, p. 1513,1516
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420
[4] Patent: EP1475368, 2004, A1. Location in patent: Page 57 |
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