6-Carbamoylpyridine-2-carboxylic acid → 6-Cyanopyridine-2-carboxylic acid

HRID 1397290ノート

反応式

HRID 1397290 の反応式
[C:1]([C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=1)(=O)[NH2:2]>P(Cl)(Cl)(Cl)=O>[C:1]([C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=1)#[N:2]

参加物

3

反応物 1

HCID 186766986-Carbamoylpyridine-2-carboxylic acid

生成物 1

HCID 212530396-Cyanopyridine-2-carboxylic acid収率 56.3%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

6-Carbamoylpicolinic acid (1.0 g, 6.0 mmol) was taken in phosphorus oxychloride (20 mL) and heated to reflux for 4 h. Excess POCl3 was removed under reduced pressure and the residue was quenched with ice water. The organic product was extracted with EtOAc and the solvent was removed under reduced pressure to afford 6-cyanopicolinic acid (500 mg, yield 56%), which was carried through without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.31-8.28 (m, 2H), 8.26-8.21 (m, 1H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03. found: 147.2 (M−H)−.

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customExcess POCl3 was removed under reduced pressure
  4. customthe residue was quenched with ice water
  5. extractionThe organic product was extracted with EtOAc
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-4526c5e2257a4ede8c9ab7d6bc4fa56e
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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