Methanol → 5-(4-Methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 11321

反応式

HRID 11321 の反応式
[H-].[Na+].CN(C)C=[C:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:7](=O)[CH3:8].COC(C1C(C2C=CC=CC=2Cl)C(C(OC)=O)=C(C)[NH:25][C:24]=1COCCN1C(=O)C2C(=CC=CC=2)C1=O)=O.[CH3:56]O.[CH3:58][N:59](C)[CH:60]=[O:61]>>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:6]2[CH:7]=[C:8]([C:24]#[N:25])[C:60](=[O:61])[NH:59][C:58]=2[CH3:56])=[CH:15][CH:14]=1

参加物

6

反応物 5

HCID 887MethanolHCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 112609924-(2-Chlorophenyl)-2-[[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]methyl]-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3,5-Dimethyl EsterHCID 539901024-Dimethylamino-3-(4-methoxyphenyl)-3-buten-2-one

生成物 1

HCID 133747585-(4-Methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile収率 82%

実験手順

To a stirred solution of sodium hydride (60% dispersion in mineral oil, 4.5 g, 112 mmol) in N,N-dimethylformamide (100 mL) was added dropwise at 0° C. a solution of crude 4-dimethylamino-3-(4-methoxyphenyl)-but-3-en-2-one (3) from the previous step, 2-cyano-acetamide (4, 4.75 g, 56.5 mmol) and methanol (4.54 mL, 112 mmol) in N,N-dimethylformamide (50 mL). The reaction mixture was stirred at ambient temperature for 15 min and then at 95° C. for 18 h. After cooling to ambient temperature most of the solvent was removed under reduced pressure. The residue was hydrolysed with saturated aqueous ammonium chloride solution (100 mL). The precipitated solid was collected by filtration with suction, rinsed with water and diethyl ether and dried under vacuum to give 5-(4-methoxy-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (5) as a brownish solid (10.0 g, 82% yield over two steps, 99% pure by LC-MS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.70 (s, 1H); 7.19 (m, 2H); 6.72 (m, 2H); 3.73 (s, 3H); 1.71 (s, 3H).

後処理

  1. waitat 95° C. for 18 h
  2. temperatureAfter cooling to ambient temperature most of the solvent
  3. customwas removed under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration with suction
  5. washrinsed with water and diethyl ether
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-ba1febf7ca664aec9fbf4db68eca4f2b
出典データセット
uspto-grants-2006_08
特許番号
US07098211B2

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