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

HRID 2092760노트

반응식

HRID 2092760 반응식
[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]

참가 물질

4

반응물 2

HCID 108515652-Chloro-4-iodo-nicotinic acid methyl esterHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 58317566Methyl 2-chloro-4-cyanonicotinate수율 34.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

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, 3H), 7.57 (d, J=5.37 Hz, 1H), 8.66 (d, J=4.88 Hz, 1H).

후처리

  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)

출처 및 근거

ORD 기록
ord-08a4af35a31f428ab9f89572defc817a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440689B2

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