ChemicalBook CAS DataBase List 2-(2-NITROPHENYL)ETHANAMINE

2-(2-NITROPHENYL)ETHANAMINE synthesis

12synthesis methods

Product Name:2-(2-NITROPHENYL)ETHANAMINE
CAS Number:33100-15-1
Molecular formula:C8H10N2O2
Molecular Weight:166.18

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33100-15-1
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$45.00/10mg

Yield: 100%

Reaction Conditions:

Stage #1:2-nitro-benzeneacetonitrile with dimethylsulfide borane complex in tetrahydrofuran at 0; for 8 h;Heating / reflux;
Stage #2: with methanol for 1 h;Heating / reflux;

Steps:

6.1
To a solution of (2-nitro-phenyl) -acetonitrile (6.8 g, 42 mmol) in tetrahydrofuran (120 mL) was added BORANE-METHYLSULFIDE complex (96 mmol, 48 mL of 2M in tetrahydrofuran solution) at 0 C. After addition, the resulting solution was refluxed for 8 hours. After cooling to room temperature, the reaction mixture was quenched with 50 ML of methanol. The solvent was removed, and the residue was dissolved in 50 mL of methanol and refluxed for 1 h. The solution was concentrated and dried under vacuum to give 2- (2-NITRO-PHENYL)-ETHYLAMINE. (Yield: 7.0 g, QUANTITATIVE). LH NMR (200 MHz, CDC13) : 8 7.90 (d, 1H), 7.50 (t, 1H), 7.40 (m, 2H), 3.00 (s, 4H), 1.40 (br, 2H)

References:

WARNER-LAMBERT COMPANY LLC WO2004/69245, 2004, A1 Location in patent:Page/Page column 85