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

HRID 1771633

Reaktionsgleichung

Reaktionsgleichung von HRID 1771633
[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

Komponenten

6

Edukt 1

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

Produkt 1

HCID 847848N-(3-amino-2,6-dimethylphenyl)acetamideAusbeute 19,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e7bc835ed10c4d12b461dc0aca9f5049
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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