P-Anisidine → N-(4-methoxyphenyl)pyridin-4-amine

HRID 266756

反応式

HRID 266756 の反応式
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>ClCCl>[N:6]1[CH:7]=[CH:8][C:3]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:4][CH:5]=1

参加物

4

反応物 2

HCID 7732P-AnisidineHCID 818524-Chloropyridine hydrochloride

生成物 1

HCID 3628677N-(4-methoxyphenyl)pyridin-4-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

A stirred mixture of 4-chloropyridine hydrochloride (2 g) and 4-methoxyaniline (4.9 g) was heated at 140° C. for 5 hours. After cooling the residue was dissolved in dichloromethane (250 ml), the solution extracted with water (2×100 ml). The aqueous extracts were treated with sodium hydroxide solution and then extracted with ethyl acetate (4×100 ml). The combined organic extracts were washed with water, and saturated sodium chloride solution, then dried and the solvent evaporated. Purification by flash chromatography on silica, eluting with 10% v/v methanol/dichloromethane gave 4-(4-pyridylamino)-methoxybenzene, 2 g, as a fawn solid: m.p. 159°-160° C.; NMR (d6DMSO) δ 8.47 (1H, s), 8.09 (2H, d), 7.10 (2H, d), 6.92 (2H, d), 6.70 (2H, dd), 3.73 (3H, s); m/e 201 (M+H)+ ; calculated for C12H12N2O3 : C, 72.0; H, 6.0; N, 14.0. found: C, 71.4; H, 6.1; N, 13.8%.

後処理

  1. temperatureAfter cooling the residue
  2. extractionthe solution extracted with water (2×100 ml)
  3. additionThe aqueous extracts were treated with sodium hydroxide solution
  4. extractionextracted with ethyl acetate (4×100 ml)
  5. washThe combined organic extracts were washed with water, and saturated sodium chloride solution
  6. customdried
  7. customthe solvent evaporated
  8. customPurification by flash chromatography on silica
  9. washeluting with 10% v/v methanol/dichloromethane

出典と根拠

ORDレコード
ord-ffb711b440634cc794ddb9d3d91a7c45
出典データセット
uspto-grants-1997_07
特許番号
US05652242

関連ノート

読み込み中…