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

HRID 2113629노트

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HRID 2113629 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 62652Cuprous chloride촉매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-72e3c13293b74d47861e8e846db16a5b
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432275B2

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