Ammonia → 4-[(Pyridin-4-yl)amino]phenol

HRID 266757

反応式

HRID 266757 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.N>Br>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 222AmmoniaHCID 3628677N-(4-methoxyphenyl)pyridin-4-amine

生成物 1

HCID 130984564-[(Pyridin-4-yl)amino]phenol

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

反応条件

温度
140 °C

実験手順

A mixture of the product from step (i) above (2.0 g) and 48% w/v hydrobromic acid (30 ml) was heated at 140° C. for 4 hours. The cooled solution was neutralised with 0.880 ammonia solution and then extracted four times with ethyl acetate. The combined organic extracts were washed with water and saturated sodium chloride solution, then dried (MgSO4) and evaporated. Purification by flash chromatography on silica, eluting with 10 to 20% v/v methanol/dichloromethane gave 4-(4-pyridylamino)phenol, 0.78 g as an off-white solid: m.p. 246°-248° C.; NMR (CDCl3 +d6DMSO) δ 8.92 (1H, b), 8.09 (2H, d), 7.31 (1H, s), 7.00 (2H, d), 6.79 (2H, d), 6.67 (2H, dd); m/e 187 (M+H)+.

後処理

  1. extractionextracted four times with ethyl acetate
  2. washThe combined organic extracts were washed with water and saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica
  6. washeluting with 10 to 20% v/v methanol/dichloromethane

出典と根拠

ORDレコード
ord-a737062066b54e3481095b72f2073ca3
出典データセット
uspto-grants-1997_07
特許番号
US05652242

関連ノート

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