Pyridine → 3-(3-Chloro-4-methoxyphenyl)propan-1-amine

반응식

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.S(Cl)([Cl:14])(=O)=O.[N:16]1C=CC=[CH:18][CH:17]=1>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][CH2:18][CH2:17][NH2:16])=[CH:5][C:4]=1[Cl:14]

참가 물질

반응물 3

HCID 1049Pyridine

HCID 24648Sulfuryl chloride

HCID 312444-Methoxybenzaldehyde

생성물 1

HCID 122776873-(3-Chloro-4-methoxyphenyl)propan-1-amine수율 77%

실험 절차

4-Methoxy-benzaldehyde (Aldrich) (42 g, 0.31 mole) and pyridine (0.6 ml, catalytic) were stirred together under nitrogen and sulfuryl chloride (51 g, 0.37 mole) added over 30 min, maintaining the internal temperature of the reaction at between 25 and 30° C. There was a vigorous evolution of gas. The mixture was stirred at room temperature for a further 30 min, and then warmed to 70° C. for 4 h. Excess reagents were removed by evaporation in vacuo and the residue taken up in 50 ml diisopropyl ether and poured onto 500 ml hexane with vigorous stirring, from which the product precipitates. The solid was filtered off and washed with hexane and then dried in vacuo to give the title product (40.3 g, 77%), m.p. 55-56° C.; 1HNMR (400 MHz, CDCl3) δ: 3.99 (s, 3H), 7.05 (dd, 1H), 7.91 (d, 1H), 9.86 (s, 1H); Anal. Found: C, 56.13; H, 4.14%. C8H7ClO2 requires C, 56.33; H, 4.14%.