ETHYL 3-AMINO-4-(METHYLAMINO)BENZOATE synthesis
- Product Name:ETHYL 3-AMINO-4-(METHYLAMINO)BENZOATE
- CAS Number:66315-23-9
- Molecular formula:C10H14N2O2
- Molecular Weight:194.23
71254-71-2
66315-23-9
Step 1-1-3 Synthesis of ethyl 3-amino-4-methylaminobenzoate: Ethyl 4-methylamino-3-nitrobenzoate (6.80 g, 30.3 mmol) prepared in Step 1-1-2 was dissolved in methanol (200 mL), and 5% palladium carbon catalyst (1.10 g) was added to the solution. The reaction mixture was stirred overnight at room temperature under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford ethyl 3-amino-4-methylaminobenzoate (4.85 g, 82% yield) as a light brown powder. The product was characterized by 1H-NMR (CDCl3): δ 7.92 (dd, J = 1.9, 8.5 Hz, 1H), 7.40 (d, J = 1.9 Hz, 1H), 6.58 (d, J = 8.5 Hz, 1H), 4.31 (q, J = 7.3 Hz, 2H), 3.99 (brs, 1H), 3.22 (brs, 2H), and 2.19 (s, 3H), 1.36 (t, J = 7.3 Hz, 3H). Mass spectral analysis showed m/z: 194 (M+, base peak), 149.
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Yield: 88%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in methanol;ethanol at 20; under 3102.97 Torr; for 5 h;Inert atmosphere;Time;
Steps:
1h.e; 1i.e Step-e:
Step-e:
Synthesis of ethyl 3-amino-4-(methylamino)benzoate (1e)
To a solution of ethyl 4-(methylamino)-3-nitrobenzoate (13.0 g, 58 mmol) in methanol (180 mL) was added slurry of 10% Pd/C (1.3 g in 10 mL of ethanol) under nitrogen atmosphere.
The flask was kept in a Parr shaker at RT under hydrogen pressure (60 psi) for 5 h.
The reaction mixture was filtered through celite bed and concentrated under vacuum to afford the title compound (10.0 g, 88%); 1H NMR (400 MHz, DMSO-d6): δ 7.23 (dd, J=1.6 Hz, J=8.4 Hz 1H), 7.16 (d, J=1.6 Hz, 1H), 6.39 (d, J=8.4 Hz, 1H), 5.38-5.37 (m, 1H), 4.66 (s, 2H), 4.18 (q, J=7.2 Hz, 2H), 2.77 (d, J=5.2 Hz, 3H), 1.26 (t, J=7.2 Hz, 3H); LC-MS: m/z 195.1 (M-1)+.
References:
Mitobridge Inc.;Biddle, Margaret;Kluge, Arthur;Sasmal, Sanjita;Lagu, Bharat;Wu, Xinyuan;Ogiyama, Takashi;Bell, Eric US10766888, 2020, B1 Location in patent:Page/Page column 21
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