4-Methyl-3-nitroaniline → N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide

HRID 1921285

Reaktionsgleichung

Reaktionsgleichung von HRID 1921285
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([C:15](O)=[O:16])[CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:15]([CH:12]2[CH2:14][CH2:13]2)=[O:16])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Komponenten

7

Edukt 4

HCID 83904-Methyl-3-nitroanilineHCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 4104437N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamideAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (4-methyl-3-nitrophenyl)amine (304 mg) in DMF (3 mL) were added cyclopropanecarboxylic acid (258 mg), HATU (1.14 g) and iPr2NEt (1.55 g) successively, and the mixture was stirred at room temperature for 16 hr under a nitrogen atmosphere. The reaction mixture was diluted with EtOAc (15 mL) and the resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with EtOAc-hexane (1:2) to give N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide (413 mg).

Aufarbeitung

  1. washthe resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with EtOAc-hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-bca658655c604b3d9c42e3007194f17b
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173684B2

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