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

HRID 1044136ノート

反応式

HRID 1044136 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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 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.

後処理

  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. washThe obtained solid was rinsed with iPr2O-hexane

出典と根拠

ORDレコード
ord-d259c30265c545ce8dbc1b63868907eb
出典データセット
uspto-grants-2013_10
特許番号
US08563575B2

反応ノート

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