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Methyl 2-methyl-5-nitrobenzoate (5.0 g, 25.6 mmol) was dissolved in [ETOH] with Raney nickel under a 35 psi atmosphere of H2. The reaction was stirred for 20 h, then filtered through Celite washed with [MEOH] and concentrated in vacuo to afford 4.2 g (100percent) of methyl [5-AMINO-2-METHYLBENZOATE.]
99%
With hydrogen In ethyl acetate at 23℃; for 16 h;
5-Amino-2-methylbenzoic Acid Methyl Ester (41). To a solution of nitro 35 (635 mg, 3.3 mmol) in EtOAc (10 mL) was added 10percent Pd-C (30 mg) and it was allowed to stir for 16 h at 23° C. under H2 atmosphere. The reaction was filtered through a celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to furnish compound 41 (536 mg, >99percent) as a colorless oil, Rf=0.57 (hexane:EtOAc=1:1). 1HNMR(400 MHz, CDCl3): δ 7.21 (d, 1H, J=2.5 Hz), 6.97 (d, 1H, J=8.1 Hz), 6.69 (dd, 1H, J=2.5 and 8.1 Hz), 3.82 (s, 3H), 3.64 (s, 2H), 2.43 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 168.1, 144.1, 132.3, 129.8, 129.5, 118.8, 116.7, 51.6, 20.6. MS (EI): m/z 165.20 [M]+. HRMS (EI), calcd for C9H11NO2165.0790, found [M]+ 165.0787.
86%
With hydrogen In methanol at 80℃; for 14 h;
6.3 g (32 mmol) of methyl 2-methyl-5-nitrobenzoate are dissolved in 80 ml of anhydrous methanol and then transferred into a steel reactor. The mixture is degassed with nitrogen and then 630 mg of Pd/C (5percent) are added. The reaction medium is then subjected to a hydrogen pressure of 4 bar and to a temperature of 80° C. for 14 hours and then brought to ambient pressure and temperature and filtered. The residue, after evaporation, is purified by chromatography on a silica column. A brown oil is obtained (m=4.6 g, Y=86percent).
860 mg
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 3 h;
153.1 5-Amino-2-methyl-benzoic acid methyl ester To a solution of 2-methyl-5-nitrobenzoic acid methyl ester (1015 mg) in EtOH (33 mL) was added 10percent palladium on charcoal (175 mg) and the reaction mixture was stirred under an atmospheric pressure of hydrogen for 3 h at RT. It was filtered over a pad of celite and the filtrate was concentrated in vacuo to give 860 mg of the titled compound as an orange oil. 1H NMR (CDCl3) δ: 7.27 (d, J=2.6 Hz, 1H), 7.05 (d, J=8.1 Hz, 1H), 6.77 (dd, J1=8.1 Hz, J2=2.6 Hz, 1H), 3.89 (s, 3H), 3.64 (s, 2H), 2.49 (s, 3H)
Reference：
[1] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12074 - 12075
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
[3] Patent: WO2004/18414, 2004, A2, . Location in patent: Page 110
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5228 - 5240
[5] Patent: US2011/269834, 2011, A1, . Location in patent: Page/Page column 29
[6] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 635 - 654
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 634 - 639
[8] Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 2176 - 2186
[9] Tetrahedron, 2008, vol. 64, # 14, p. 3253 - 3267
[10] Patent: US6689922, 2004, B1, . Location in patent: Page column 86
[11] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[12] Patent: US2005/43385, 2005, A1, . Location in patent: Page/Page column 14
[13] Patent: WO2006/63805, 2006, A1, . Location in patent: Page/Page column 76
[14] Patent: WO2007/71955, 2007, A1, . Location in patent: Page/Page column 52
[15] Patent: US2009/239859, 2009, A1, . Location in patent: Page/Page column 298
[16] Patent: WO2005/9940, 2005, A1, . Location in patent: Page 175
[17] Patent: US2010/81643, 2010, A1, . Location in patent: Page/Page column 37
[18] Patent: WO2010/47982, 2010, A1, . Location in patent: Page/Page column 78
[19] Patent: WO2012/114268, 2012, A1, . Location in patent: Page/Page column 134
[20] Patent: US2014/73651, 2014, A1, . Location in patent: Paragraph 0984; 0985
2
[ 1975-52-6 ]
[ 18595-12-5 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
[2] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12074 - 12075
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 635 - 654
[4] Patent: US2011/269834, 2011, A1,
3
[ 18583-89-6 ]
[ 83140-97-0 ]
[ 18595-12-5 ]
Reference：
[1] Patent: US5234946, 1993, A,
4
[ 18595-12-5 ]
[ 421551-82-8 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
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