Ethyl Acetate → 3-(3-chloro-1H-pyrazol-1-yl)pyridine

HRID 57091

反応式

HRID 57091 の反応式
Cl.[Cl:2][C:3]1[CH:7]=[C:6](C(O)=O)[N:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1.C(OCC)(=O)C>CN(C)C=O.[OH-].[NH4+].O.[Cu]=O>[Cl:2][C:3]1[CH:7]=[CH:6][N:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1

参加物

7

反応物 2

HCID 8857Ethyl AcetateHCID 1180217823-Chloro-1-(pyridine-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride

生成物 1

HCID 674995403-(3-chloro-1H-pyrazol-1-yl)pyridine収率 73.4%

試薬・触媒・溶媒 4

HCID 14829Copper oxide触媒2 回HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
120 °C

実験手順

3-Chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride (1.00 g, 3.65 mmol) was stirred in N,N-dimethylformamide (10 mL). Copper(II) oxide (58.0 mg, 0.730 mmol) was added and the reaction was heated at 120° C. for 16 hours, at which point the reaction was ˜20% complete. Additional copper(II) oxide (112 mg, 1.46 mmol) was added and the reaction was stirred for 5 hours, at which point the reaction was complete by thin layer chromatography (TLC) [Eluent: ethyl acetate]. The mixture was diluted with ammonium hydroxide (NH4OH) and water and extracted with ethyl acetate. The organic layer was washed with 15% lithium chloride and concentrated to provide an orange solid. The residue was purified by flash column chromatography using ethyl acetate as eluent and the pure fractions were concentrated to afford the desired product as a white solid (481 mg, 69.7%). The spectral characterization was in agreement with the product prepared previously.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 15% lithium chloride
  3. concentrationconcentrated
  4. customto provide an orange solid
  5. customThe residue was purified by flash column chromatography
  6. concentrationthe pure fractions were concentrated

出典と根拠

ORDレコード
ord-e057a9d09fff4e41a0af34e569f9968e
出典データセット
uspto-grants-2016_09
特許番号
US09434712B2

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