Hydrochloric Acid → 5-Chloro-6-methylpyridine-2-carbonitrile

HRID 530801Notes

Reaction equation

HRID 530801 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8].[ClH:11]>CC#N.Cl[Cu]>[Cl:11][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 552529845-Amino-6-methylpicolinonitrile

Product 1

HCID 573365975-Chloro-6-methylpyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-amino-6-methylpicolinonitrile (2) (260 mg, 1.95 mmol), CuCl (290 mg, 2.93 mmol) and t-BuONO (456 mg, 3.9 mmol) in CH3CN (10 mL) was stirred at room temperature under N2 for 2 h, and then warmed to 60° C. After 2 h, 10 mL 6N HCl was added and extracted with EA (3×10 mL). The organic phase was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by Prep-TLC using PE/EtOAc=1/1 to give title compound as oil.

Workup

  1. extractionextracted with EA (3×10 mL)
  2. dry with materialThe organic phase was dried with anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Prep-TLC

Sources & evidence

ORD record
ord-9f23e741220f48faaf969e926c077df4
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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