N-(2,6-dimethyl-3-nitrophenyl)acetamide → N-(3-amino-2,6-dimethylphenyl)acetamide

HRID 1771633

反応式

HRID 1771633 の反応式
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[NH:12][C:13](=[O:15])[CH3:14]>CO.CCO.C(O)(=O)C.[Pd]>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([NH:12][C:13](=[O:15])[CH3:14])[C:4]([CH3:11])=[CH:5][CH:6]=1

参加物

6

反応物 1

HCID 223591N-(2,6-dimethyl-3-nitrophenyl)acetamide

生成物 1

HCID 847848N-(3-amino-2,6-dimethylphenyl)acetamide収率 19.3%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

N-(2,6-dimethyl-3-nitro-phenyl)acetamide (12 g, 58 mmol, 1.0 eq) was dissolved in a mixture of MeOH (60 mL), EtOH (30 mL) and acetic acid (60 mL). Pd/C (1.6 g, 10%) was added and the reaction stirred at room temperature under H2 for 36 h. The catalyst was removed by filtration through celite and the filtrate collected. Water was added and the pH adjusted to pH 8 by addition of aqueous NaHCO3. The solution was concentrated in vacuo to remove methanol and ethanol. The aqueous layer was extracted with EtOAc and the combined organic extracts were dried (Na2SO4) filtered and evaporated in vacuo. The crude product was purified by column chromatography (EtOAc:petroleum ether, 1:10 to 1:1) to give the title compound as a yellow solid (2 g, 19%).

後処理

  1. customThe catalyst was removed by filtration through celite
  2. customthe filtrate collected
  3. additionWater was added
  4. additionthe pH adjusted to pH 8 by addition of aqueous NaHCO3
  5. concentrationThe solution was concentrated in vacuo
  6. customto remove methanol and ethanol
  7. extractionThe aqueous layer was extracted with EtOAc
  8. dry with materialthe combined organic extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe crude product was purified by column chromatography (EtOAc:petroleum ether, 1:10 to 1:1)

出典と根拠

ORDレコード
ord-e7bc835ed10c4d12b461dc0aca9f5049
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

関連ノート

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