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

HRID 22922

反応式

HRID 22922 の反応式
[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]

参加物

4

反応物 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 312444-Methoxybenzaldehyde

生成物 1

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

実験手順

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%.

後処理

  1. temperaturemaintaining
  2. customthe internal temperature of the reaction at between 25 and 30° C
  3. temperaturewarmed to 70° C. for 4 h
  4. customExcess reagents were removed by evaporation in vacuo
  5. additionpoured onto 500 ml hexane with vigorous stirring, from which the product
  6. customprecipitates
  7. filtrationThe solid was filtered off
  8. washwashed with hexane
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-ed79363d7c4b4e89bde6a718f51e6b66
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

関連ノート

読み込み中…