Cesium carbonate → N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine

HRID 1429888ノート

反応式

HRID 1429888 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:12]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:25][CH:26]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 796132-Chloro-3-nitropyridineHCID 27238314-Benzyloxyaniline hydrochloride

生成物 1

HCID 40676934N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine収率 75%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-chloro-3-nitropyridine (2.0 g), 4-(benzyloxy)aniline hydrochloride (3.6 g), and cesium carbonate (12.3 g) in NMP (50 mL) was heated at 100° C. for 5 h. After cooling to rt, the mixture was partitioned between AcOEt and H2O. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography (SiO2, hexane/AcOEt=1/1) to give N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine (3.04 g) as a brown solid.

後処理

  1. temperatureAfter cooling to rt
  2. customthe mixture was partitioned between AcOEt and H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, hexane/AcOEt=1/1)

出典と根拠

ORDレコード
ord-8d05bbf02fac42b694f7c4298ed69ca8
出典データセット
uspto-grants-2015_01
特許番号
US08940758B2

反応ノート

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