Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate synthesis
- Product Name:Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate
- CAS Number:214470-60-7
- Molecular formula:C11H14ClNO4
- Molecular Weight:259.69
214470-58-3
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214470-60-7
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Yield:214470-60-7 99%
Reaction Conditions:
with 10% Pd/C;hydrogen in ethyl acetate; for 12 h;
Steps:
2-Amino-4-(2-chloro-ethoxy)-5-methoxy-benzoic acid methyl ester.
To a solution of 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoic acid methyl ester (2.7 g, 9.32 mmol) in EtOAc (30 mL) was added 10% Pd/C (405 mg) and the mixture was stirred under H2 for 12 h. The mixture was filtered through Celite washing with EtOAc and the filtrate was concentrated to dryness to afford 2-amino-4-(2-chloroethoxy)-5-methoxybenzoic acid methyl ester as a solid (2.40g, 99%). 1H NMR (300 MHz, DMSO-d6) δ 7.15 (s, 1H), 6.40 (s, 2H), 6.35 (s, 1H), 4.18 (t, 2H), 3.95 (t, 2H), 3.70 s, 3H), 3.65 (s, 3H), LC-MS (ESI) m/z 260 (M+H)+.
References:
Holladay, Mark W.;Campbell, Brian T.;Rowbottom, Martin W.;Chao, Qi;Sprankle, Kelly G.;Lai, Andiliy G.;Abraham, Sunny;Setti, Eduardo;Faraoni, Raffaella;Tran, Lan;Armstrong, Robert C.;Gunawardane, Ruwanthi N.;Gardner, Michael F.;Cramer, Merryl D.;Gitnick, Dana;Ator, Mark A.;Dorsey, Bruce D.;Ruggeri, Bruce R.;Williams, Michael;Bhagwat, Shripad S.;James, Joyce [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 18,p. 5342 - 5346] Location in patent:supporting information; experimental part
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