Ammonium formate → 4-(3-Methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline

HRID 518802ノート

反応式

HRID 518802 の反応式
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([O:22][CH:23]([CH3:25])[CH3:24])[CH:14]=1>CO.[Pd]>[CH3:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([O:22][CH:23]([CH3:25])[CH3:24])[CH:14]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 866979683-Methoxy-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine

生成物 1

HCID 866979734-(3-Methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline収率 103.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

7.55 g of ammonium formate and 1.5 g of Pd/C (10%) are added to a solution of 5.75 g of 3-methoxy-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine in 100 ml of methanol. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel, and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure. The residue is taken up with 60 ml of ethyl acetate and 20 ml of water. The 2 phases are separated, and the aqueous phase is extracted with twice 20 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated, so as to give 5.35 g of 4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline in the form of a brown gum.

後処理

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customThe 2 phases are separated
  5. extractionthe aqueous phase is extracted with twice 20 ml of ethyl acetate
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-cc295b7e7f1049699e53cb41c69d335b
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

読み込み中…