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

HRID 266757

반응식

HRID 266757 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

반응 조건

온도
140 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a737062066b54e3481095b72f2073ca3
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05652242

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