Dimethylcarbamoyl Chloride → Methyl 2-cyanopyridine-4-carboxylate

HRID 1397282

反応式

HRID 1397282 の反応式
C[Si]([C:5]#[N:6])(C)C.[CH3:7]N(C)C(Cl)=O.C[C:14]1[CH:22]=[N+:21]([O-])[CH:20]=[CH:19][C:15]=1[C:16]([O-:18])=[O:17]>C(Cl)Cl>[C:5]([C:20]1[CH:19]=[C:15]([CH:14]=[CH:22][N:21]=1)[C:16]([O:18][CH3:7])=[O:17])#[N:6]

参加物

5

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 53443469Methylisonicotinate N-oxide

生成物 1

HCID 12132796Methyl 2-cyanopyridine-4-carboxylate収率 33.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trimethylsilyl cyanide (3.8 g, 0.0386 mol) and dimethylcarbamyl chloride (5.0 g, 0.0483 mol) were added to a solution of methylisonicotinate N-oxide (5.0 g, 0.0322 mol) in dry CH2Cl2 (50 mL) at room temperature. The reaction mixture was stirred at room temperature for 12 h and then quenched with 10% K2CO3 solution. The organic product was extracted with CH2Cl2 and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica 230-400 mesh, eluent 1-2% MeOH in CH2Cl2) to afford methyl 2-cyanoisonicotinate (1.75 g, yield 33%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.97-8.95 (d, J=5.0 Hz, 1H), 8.41 (m, 1H), 8.15-8.13 (dd, J=4.8 Hz, 1.6 Hz, 1H), 3.92 (s, 3H).

後処理

  1. customquenched with 10% K2CO3 solution
  2. extractionThe organic product was extracted with CH2Cl2
  3. washthe organic layer was washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash column chromatography (silica 230-400 mesh, eluent 1-2% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-3f60376d71ec48baad29d7c1ceb9a5a3
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

関連ノート

読み込み中…