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ChemicalBook CAS DataBase List 4-broMo-N1-Methylbenzene-1,2-diaMine
69038-76-2

4-broMo-N1-Methylbenzene-1,2-diaMine synthesis

5synthesis methods
4-bromo-N-methyl-2-nitroaniline

53484-26-7

4-broMo-N1-Methylbenzene-1,2-diaMine

69038-76-2

General procedure for the synthesis of 4-bromo-N1-methylbenzene-1,2-diamine from 4-bromo-N-methyl-2-nitroaniline: to a solution of 4-bromo-N-methyl-2-nitroaniline (2.1 g, 9 mmol) in methanol (MeOH, 50 mL) was added iron powder (Fe, 2.5 g, 45 mmol) and ammonium chloride (NH4Cl, 4.8 g, 90 mmol). The reaction mixture was stirred at 80 °C for 4 hours. After completion of the reaction, the mixture was poured into water (H2O, 60 mL) and extracted with ethyl acetate (EA, 40 mL × 2). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give 4-bromo-N1-methylbenzene-1,2-diamine (2.0 g, 99% yield) as a yellow solid.LC-MS m/z: 203.1 [M + H]+. Retention time (tR) = 1.64 min.

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Yield: 99%

Reaction Conditions:

with iron;ammonium chloride in methanol at 80; for 4 h;

Steps:


To a solution of 4-bromo-N-methyl-2-nitroaniline (2.1 g, 9 mmol) in MeOH (50mL) was added Fe powder (2.5 g, 45 mmol) and NH4C1 (4.8 g, 90 mmol). The mixture wasstirred at 80 °C for 4 h, poured into H20 (60 mL) and extracted with EA (40 mL x 2). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 4-bromo-N’-methylbenzene-1,2-diamine (2.0 g, 99 %) as a yellow solid. LC-MS m/z: 203.1 [M+Hj . tR = 1.64 min

References:

LYSOSOMAL THERAPEUTICS INC.;SKERLJ, Renato, T.;BOURQUE, Elyse Marie Josee;LANSBURY, Peter, T.;GOOD, Andrew, C. WO2017/176960, 2017, A1 Location in patent:Paragraph 00743