HCID 58577742、化合物 → N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine

HRID 82618ノート

反応式

HRID 82618 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][C:19]([CH3:25])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.C1COCC1.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][C:19]([CH3:25])=[CH:18][N:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 1

HCID 58577742HCID 58577742、化合物

生成物 1

HCID 58577457N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine収率 52%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of N-[4-(benzyloxy)phenyl]-5-methyl-3-nitropyridin-2-amine (1.33 g) in acetic acid (10 mL) and THF (10 mL) was added zinc (2.59 g) at 0° C., and the mixture was stirred at 0° C. for 2 h. After stirring at room temperature overnight, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with AcOEt, washed with sat. NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 5%-50% AcOEt in hexane) to give N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine (0.63 g) as a blue solid.

後処理

  1. stirringAfter stirring at room temperature overnight
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with AcOEt
  5. washwashed with sat. NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (NH silica gel, eluted with 5%-50% AcOEt in hexane)

出典と根拠

ORDレコード
ord-97679bc12ab14838a248ece99a3f0949
出典データセット
uspto-grants-2014_09
特許番号
US08846713B2

反応ノート

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