Diethyl Malonate → 4-Hydroxy-6-oxo-2-(4-phenoxyphenyl)-1,6-dihydropyridine-3-carbonitrile

HRID 81052노트

반응식

HRID 81052 반응식
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[CH:3][C:4]#[N:5].[C:19](OCC)(=[O:26])[CH2:20][C:21](OCC)=[O:22]>>[OH:26][C:19]1[C:3]([C:4]#[N:5])=[C:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:7]=2)[NH:1][C:21](=[O:22])[CH:20]=1

참가 물질

3

반응물 2

HCID 7761Diethyl MalonateHCID 669270523-Amino-3-(4-phenoxyphenyl)acrylonitrile

생성물 1

HCID 696705204-Hydroxy-6-oxo-2-(4-phenoxyphenyl)-1,6-dihydropyridine-3-carbonitrile수율 74.1%

실험 절차

3-Amino-3-(4-phenoxyphenyl)acrylonitrile (720 mg, 3.05 mmol) in diethyl malonate (9 mL, 59.3 mmol) was microwaved at 250° C. for 10 min. After cooling to room temperature, the solid was collected by filtration, washed with 20% isopropanol in heptanes and dried under vacuum to give 4-hydroxy-6-oxo-2-(4-phenoxyphenyl)-1,6-dihydropyridine-3-carbonitrile (688 mg, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (1H, br. s), 7.67 (2H, δ, J=8.53 Hz), 7.48 (2H, t, J=7.91 Hz), 7.25 (1H, t, J=7.40 Hz), 7.11 (4H, dd, J=19.70, 8.16 Hz), 5.52-5.74 (1H, m); MS (ES+) m/z: 305 (M+H); LC retention time: 3.546 min (analytical HPLC Method A).

후처리

  1. filtrationthe solid was collected by filtration
  2. washwashed with 20% isopropanol in heptanes
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-fe850945f02d4d5592a03a66b6329218
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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