Sodium Cyanide → HCID 69480951, compound

HRID 2364215Notes

Reaction equation

HRID 2364215 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)=[CH:4][N:3]=1.[C:20]([Cu])#[N:21].[C-]#N.[Na+]>CN1C(=O)CCC1.CCOC(C)=O>[F:19][C:14]1[CH:13]=[C:12]([CH2:11][C:5]2[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:20]#[N:21])=[N:3][CH:4]=2)[CH:17]=[CH:16][C:15]=1[F:18]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 86612776HCID 86612776, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69480951HCID 69480951, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 2-chloro-5-[(3,4-difluorophenyl)methyl]-3-nitropyridine (10.88 g, 38.22 mmol) in NMP (50 ml), was added CuCN (10.27 g, 0.115 mmol) and NaCN (1.02 g). Heated in the microwave at 170° C. for 1 h and the resulting mixture was diluted with EtOAc and filtered through Celite. Water was added to the filtrate and the organic layer was washed with water and brine, dried and concentrated in vacuo. The resulting product was purified by chromatography on silica gel, eluting with 0-25% EtOAc/hexanes to afford an amber oil. 1H NMR (CDCl3) δ 8.82 (1H, s), 8.31 (1H, s), 7.22-7.15 (1H, m), 7.03-6.98 (1H, m), 6.94-6.90 (1H, m), 4.16 (2H, s).

Workup

  1. filtrationfiltered through Celite
  2. additionWater was added to the filtrate
  3. washthe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe resulting product was purified by chromatography on silica gel
  7. washeluting with 0-25% EtOAc/hexanes
  8. customto afford an amber oil

Sources & evidence

ORD record
ord-7707fbbd8f2a4bb3bf49e9a6b8f6cb05
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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