Methyl 2-chloro-4-methylpyridine-3-carboxylate → HCID 44191036, 화합물

HRID 1959595노트

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HRID 1959595 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[N:6][C:5]=1Cl.[C:13]([Cu])#[N:14]>CN1C(=O)CCC1.O.Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[N:6][C:5]=1[C:13]#[N:14]

참가 물질

6

반응물 2

HCID 17862852Methyl 2-chloro-4-methylpyridine-3-carboxylateHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 44191036HCID 44191036, 화합물

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
180 °C

실험 절차

A suspension of 2-chloro-4-methyl-nicotinic acid methyl ester (2.64 g, 14.3 mmol) and CuCN (6.4 g, 71 mmol) in NMP (5.3 mL) was heated to 180° C. for 30 min. The reaction mixture was then cooled to room temperature and diluted with water (80 mL). After vigorous stirring for 16 h, the suspension was centrifuged and the precipitate suspended in a solution of FeCl3.6H2O (5.8 g, 21 mmol) in aqueous HCl (4 M, 80 mL). After vigorous stirring for 1 h, the suspension was extracted with DCM (3×70 mL). The organic layer was dried over Na2SO4/Na2CO3, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with EA/DCM 1:10) to give the title compound. MS (m/z): 177.0 [M+H+].

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. stirringAfter vigorous stirring for 1 h
  3. extractionthe suspension was extracted with DCM (3×70 mL)
  4. dry with materialThe organic layer was dried over Na2SO4/Na2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (elution with EA/DCM 1:10)

출처 및 근거

ORD 기록
ord-6a78b9ce9b50444dbcef6d6cb0eafb9d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410134B2

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