ChemicalBook CAS DataBase List 6-P-TOLYLPYRIDIN-3-YLAMINE

6-P-TOLYLPYRIDIN-3-YLAMINE synthesis

6synthesis methods

Product Name:6-P-TOLYLPYRIDIN-3-YLAMINE
CAS Number:170850-45-0
Molecular formula:C12H12N2
Molecular Weight:184.24

131941-26-9

170850-45-0

4.3.1 Synthesis of 4'-methyl-4-aminobiphenyl (4a): 5-nitro-2-(p-tolyl)pyridine (3a, 2.54 mmol, 541 mg) was dissolved in a solvent mixture of EtOH/EtOAc (1:1, 50 mL). The hydrogenation-reduction reaction was carried out in all-hydrogen mode in the presence of Raney Nickel catalyst at a reaction temperature of 65 °C and a hydrogen flow rate of 0.8 mL/min. Upon completion of the reaction, the resulting solution was concentrated under reduced pressure to give 480 mg of yellow solid. The crude product was purified by silica gel column chromatography using hexane/CH2Cl2 (1:1) as eluent, resulting in 440 mg of the pure target product 4'-methyl-4-aminobiphenyl (4a) as an off-white solid in 95% yield.

131941-26-9
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170850-45-0
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Yield: 99%

Reaction Conditions:

with nickel in ethanol;ethyl acetate at 65;

Steps:

3.2 General procedure for the nitro group reduction
General procedure: 4.3.1 4'-Methyl-4-aminobiphenyl (4a) Compound 3a (2.54 mmol, 541 mg) was dissolved in an EtOH/EtOAc 1:1 mixture (50 mL) and reduced by hydrogenation catalysed by Raney Nickel in an H-Cube at 65 °C at a flow rate of 0.8 mL/min, using full hydrogen mode. The solution obtained was concentrated under reduced pressure to give 480 mg of a yellow solid, which was purified by chromatography on silica gel, hexane/CH₂Cl₂ 1:1, to give 440 mg of the pure expected product as an off-white solid (95% yield).

References:

Baltus, Christine B.;Press, Neil J.;Antonijevic, Milan D.;Tizzard, Graham J.;Coles, Simon J.;Spencer, John [Tetrahedron,2012,vol. 68,# 45,p. 9272 - 9277]

13534-97-9 Synthesis