Methyl 2-chloro-4-methylpyridine-3-carboxylate → HCID 44191036、化合物

HRID 1959595ノート

反応式

HRID 1959595 の反応式
[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]

参加物

6

反応物 2

HCID 17862852Methyl 2-chloro-4-methylpyridine-3-carboxylateHCID 178418546HCID 178418546、化合物

生成物 1

HCID 44191036HCID 44191036、化合物

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
180 °C

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-6a78b9ce9b50444dbcef6d6cb0eafb9d
出典データセット
uspto-grants-2013_04
特許番号
US08410134B2

反応ノート

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