Calcium Chloride → N2-[4-(benzyloxy)phenyl]pyridine-2,3-diamine

HRID 587433노트

반응식

HRID 587433 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Ca+2]>CCO.O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 2

HCID 5284359Calcium ChlorideHCID 40676934N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine

생성물 1

HCID 28846536N2-[4-(benzyloxy)phenyl]pyridine-2,3-diamine수율 73.5%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine (1.5 g), Fe (2.6 g), and CaCl2 (260 mg) in EtOH (30 mL) and H2O (6.0 mL) was heated at 100° C. for 6 h. After cooling to rt, the precipitate was removed by Celite, and the filtrate was concentrated. The residue was partitioned between AcOEt and sat.NaHCO3aq. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography (SiO2, hexane/AcOEt=3/2 to 1/1). The is obtained solid was rinsed with iPr2O-hexane to give N2-[4-(benzyloxy)phenyl]pyridine-2,3-diamine (1.0 g) as a pale pink solid.

후처리

  1. temperatureAfter cooling to rt
  2. customthe precipitate was removed by Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between AcOEt and sat.NaHCO3aq
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by column chromatography (SiO2, hexane/AcOEt=3/2 to 1/1)
  9. customThe is obtained solid
  10. washwas rinsed with iPr2O-hexane

출처 및 근거

ORD 기록
ord-6f9631b6b0024dfb99a2a19a7a357089
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226921B2

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