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

HRID 2113629Notes

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-72e3c13293b74d47861e8e846db16a5b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432275B2

Reaction notes

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