Quinoline → 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

HRID 270571

反応式

HRID 270571 の反応式
P(Cl)(Cl)([Cl:3])=O.N1C2C(=CC=CC=2)C=CC=1.[N+:16]([C:19]1[C:20](O)=[N:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)([O-:18])=[O:17].C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:3][C:20]1[C:19]([N+:16]([O-:18])=[O:17])=[CH:24][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:22][N:21]=1

参加物

6

反応物 4

HCID 7047QuinolineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178526653HCID 178526653、化合物

生成物 1

HCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine収率 55%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a solution of phosphoryl chloride (2.0 mL, 21.2 mmol) and quinoline (1.30 mL, 10.8 mmol) was added solid powder 3-nitro-5-(trifluoromethyl)pyridin-2-ol (4.00 g, 18.3 mmol) (95% purity). The resulting dark brown thick suspension was heated to reflux for 4 h and gradually turned into a very cloudy dark brown solution. After cooling to 100° C., water (11 mL) was slowly added to the mixture which was further cooled to room temperature and neutralized carefully with Na2CO3. The resulting solution was extracted with EtOAc three times. The extracts were combined, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexanes 30:70) to afford 2.28 g of desired product.

後処理

  1. temperatureThe resulting dark brown thick suspension was heated
  2. temperatureto reflux for 4 h
  3. extractionThe resulting solution was extracted with EtOAc three times
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexanes 30:70)

出典と根拠

ORDレコード
ord-1166b3494f0f4aeb967b7d823ee371ed
出典データセット
uspto-grants-2008_11
特許番号
US07449467B2

関連ノート

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