Hydrochloric Acid → 6-Chloro-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

HRID 2113629ノート

反応式

HRID 2113629 の反応式
N[C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19].N([O-])=O.[Na+].[ClH:24]>Cl[Cu]>[Cl:24][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 462029106-Amino-3'-trifluoromethyl[2,2']bipyridinyl-5-carbonitrile

生成物 1

HCID 586281896-Chloro-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

試薬・触媒・溶媒 1

HCID 62652Cuprous chloride触媒

反応条件

温度
0 °C

実験手順

Dissolve 6-amino-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carbonitrile (1.0 g, 7.6 mmol) in 12 N HCl (20 mL) and cool to 0° C. Add NaNO2 (731 mg, 10.6 mmol) in portions over the course of 15 minutes. Allow the mixture to stir for 1 hour at 0° C. Add CuCl (2.24 g, 22.7 mmol), allow the mixture to warm to room temperature and stir for 1 hour. Pour the mixture onto ice water (100 mL) and extract with EtOAc (3×100 mL);. Dry the combined organic extracts over Na2SO4 and remove the solvent under reduced pressure. Purify the crude product by silica gel chromatography eluting with EtOAc/hexane (1:1) to yield the title compound. MS 284.04 (M+1).

後処理

  1. customover the course of 15 minutes
  2. temperatureto warm to room temperature
  3. stirringstir for 1 hour
  4. additionPour the mixture onto ice water (100 mL)
  5. extractionextract with EtOAc (3×100 mL)
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. customremove the solvent under reduced pressure
  8. customPurify the crude product by silica gel chromatography
  9. washeluting with EtOAc/hexane (1:1)

出典と根拠

ORDレコード
ord-72e3c13293b74d47861e8e846db16a5b
出典データセット
uspto-grants-2008_10
特許番号
US07432275B2

反応ノート

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