Tetrahydrofuran → HCID 86616057, compound

HRID 272772

Reaction equation

HRID 272772 reaction equation
[Cl:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C[O:13][CH2:12]C1>[Ni]>[Cl:1][C:2]1[C:3]([CH2:8][NH:9][CH:12]=[O:13])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 8182583-Chloropyridine-2-carbonitrile

Product 1

HCID 86616057HCID 86616057, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
90 °C

Procedure

3-Chloro-pyridine-2-carbonitrile (0.4 g) was reduced by hydrogenation in the presence of RaNi (0.1 g) in THF/20% NH3 (5 mL) at 30 psi. The solvent was removed and the residue was treated with 88% formic acid (10 mL) and heated at 90° C. overnight. The solvent was removed under reduced pressure, and the residue was re-dissolved in EtOAc. The organic layer was washed with Na2CO3, brine, dried, and concentrated. The residue was purified by silica gel column chromatography eluting with 100% EtOAc to give 0.3 g of the title compound. MS (APCI) m/e 171 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 9.8.51-8.53 (m, 2H), 8.15 (s, 1H), 7.93 (d, J=7.98 Hz, 1H), 7.38 (dd, J=8.13, 4.16 Hz, 1H), 4.53 (d, J=5.52 Hz, 1H).

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with 88% formic acid (10 mL)
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was re-dissolved in EtOAc
  5. washThe organic layer was washed with Na2CO3, brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-98674c30f72349d3a8667cba5c07034f
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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