Tetrahydrofuran → HCID 86616057, 화합물

HRID 272772

반응식

HRID 272772 반응식
[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

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 8182583-Chloropyridine-2-carbonitrile

생성물 1

HCID 86616057HCID 86616057, 화합물

시약·촉매·용매 1

HCID 935Nickel촉매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-98674c30f72349d3a8667cba5c07034f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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