N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide → Ammonium Hydroxide

HRID 2247223ノート

反応式

HRID 2247223 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=[O:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2]>CCO.O1CCOCC1>[NH4+:11].[OH-:12].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C:6]([NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:18])[CH3:19])[CH:7]=1

参加物

5

反応物 1

HCID 21961377N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

生成物 2

HCID 14923Ammonium HydroxideHCID 21961467HCID 21961467、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

N-(2-tert-Butyl-5-nitro-phenyl)-2-dimethylamino-acetamide (25.8 g, 92 mmol) was dissolved in EtOH (1.4 L) and 1,4-dioxane (200 mL). The solution was degassed under vacuum with stirring. 10% Pd/C (2.5 g) was added (as a slurry in EtOH). The mixture was degassed again, then the reaction vessel was charged with H2 gas (balloon) and stirred overnight at RT. The reaction was filtered through Celite® with MeOH and the filtrate was concentrated under reduced pressure. The recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2:MeOH:NH4OH(aq) step gradient giving N-(5-amino-2-tert-butyl-phenyl)-2-dimethylamino-acetamide as a brown solid.

後処理

  1. customThe solution was degassed under vacuum
  2. addition10% Pd/C (2.5 g) was added (as a slurry in EtOH)
  3. customThe mixture was degassed again
  4. additionthe reaction vessel was charged with H2 gas (balloon)
  5. stirringstirred overnight at RT
  6. filtrationThe reaction was filtered through Celite® with MeOH
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2

出典と根拠

ORDレコード
ord-9de04c4e873944d1861a2ac848fec68c
出典データセット
uspto-grants-2010_03
特許番号
US07687643B2

反応ノート

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