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

HRID 266756

반응식

HRID 266756 반응식
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

참가 물질

4

반응물 2

HCID 7732P-AnisidineHCID 818524-Chloropyridine hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
140 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-ffb711b440634cc794ddb9d3d91a7c45
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05652242

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