2-Methoxy-5-nitroaniline → N-(2-methoxy-5-nitrophenyl)propanamide

HRID 240917

Reaktionsgleichung

Reaktionsgleichung von HRID 240917
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH:5][C:20](=[O:23])[CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 74472-Methoxy-5-nitroanilineHCID 8471TriethylamineHCID 62324Propionyl chloride

Produkt 1

HCID 2176144N-(2-methoxy-5-nitrophenyl)propanamideAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-methoxy-5-nitroaniline (1) (10.1 g, 60.0 mmol) in 250 mL dichloromethane at 0°-5° C. was treated with triethylamine (10.0 g, 100.0 mmol) and propionyl chloride (6.7 g, 6.3 mL, 72.0 mmol) for 1 hour and 0.5 h at room temperature (RT). Normal aqueous workup and removal of solvent gave a light yellow solid which was washed with hexane/EtOAc (9:1) to yield solid N-(2-Methoxy-5-nitro-phenyl)-propionamide (2) (13.2 g, 98%).

Aufarbeitung

  1. customNormal aqueous workup and removal of solvent
  2. customgave a light yellow solid which
  3. washwas washed with hexane/EtOAc (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-f027d2a09ee44c4cb92ff0e7f92ae1ce
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648104B2

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