Phosphorus oxychloride → 4-Chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile

HRID 81064

반응식

HRID 81064 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[C:13]([C:29]#[N:30])[C:12](=O)[CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:34])=O>>[Cl:34][C:12]1[C:13]([C:29]#[N:30])=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[N:15]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:11]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 696704156-(4-Nitrophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile

생성물 1

HCID 669270004-Chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile수율 62%

반응 조건

온도
95 °C

실험 절차

A mixture of 6-(4-nitrophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile (211 mg, 0.515 mmol) and phosphoryl trichloride (1 mL, 10.92 mmol) was heated to 95° C. for 30 min, then concentrated. The residue was dissolved in dichloromethane (2 mL) and washed with saturated sodium bicarbonate. Silica gel chromatography, eluting with 0-100% ethyl acetate in hexanes, gave 4-chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile as white solid (136.3 mg, 62% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.35-8.41 (2H, m), 8.27-8.33 (2H, m), 8.00-8.06 (2H, m), 7.91 (1H, s), 7.38-7.46 (2H, m), 7.21 (1H, t, J=7.40 Hz), 7.10-7.18 (4H, m); MS (ES+) m/z: 428 (M+14); LC retention time: 4.141 min (analytical HPLC Method A).

후처리

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (2 mL)
  3. washwashed with saturated sodium bicarbonate
  4. washSilica gel chromatography, eluting with 0-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-23270db75bcb46e8b2aafde366cd98dc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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