2-Chloro-4-iodo-nicotinic acid methyl ester → Methyl 2-chloro-4-cyanonicotinate

HRID 515992ノート

反応式

HRID 515992 の反応式
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8](I)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([Cu])#[N:14]>CC(N(C)C)=O>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

4

反応物 2

HCID 108515652-Chloro-4-iodo-nicotinic acid methyl esterHCID 178418546HCID 178418546、化合物

生成物 1

HCID 58317566Methyl 2-chloro-4-cyanonicotinate収率 34.5%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

A solution of methyl 2-chloro-4-iodonicotinate (3.20 g, 10.76 mmol) and cyanocopper (0.963 g, 10.76 mmol) in DMA (40 mL) was stirred at 140° C. overnight. Following reaction, the mixture was filtered through Celite and the filtrate was diluted with H2O and EtOAc. The aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1) to give the title compound as a white solid (730 mg, 34.5%). 1H NMR (500 MHz, CDCl3) δ ppm 4.07 (s, 3 H), 7.57 (d, J=5.37 Hz, 1 H), 8.66 (d, J=4.88 Hz, 1 H).

後処理

  1. customreaction
  2. filtrationthe mixture was filtered through Celite
  3. additionthe filtrate was diluted with H2O and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1)

出典と根拠

ORDレコード
ord-dd8bf3c260ad425a833911aaa6c52b2e
出典データセット
uspto-grants-2015_08
特許番号
US09108970B2

反応ノート

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