4-Nitroaniline → Butanamide, 3,3-dimethyl-N-(4-nitrophenyl)-

HRID 483097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483097
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]([CH3:18])([CH3:17])[CH2:13][C:14](Cl)=[O:15]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:14](=[O:15])[CH2:13][C:12]([CH3:18])([CH3:17])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 74754-NitroanilineHCID 815143,3-Dimethylbutanoyl chloride

Produkt 1

HCID 2924068Butanamide, 3,3-dimethyl-N-(4-nitrophenyl)-Ausbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Five grams of 4-nitroaniline was stirred in 25 ml of pyridine and 4.95 g of 3,3-dimethylbutyryl chloride was added. The mixture was stirred 15 hours and poured into ice-water. The resultant solid was collected on a filter and dissolved in 200 ml of ethyl acetate and the solution was treated with activated charcoal and concentrated to yield 6.3 g of 4-nitro-3,3-dimethylbutyrylaminobenzene, m.p. 192°-194°. This material was reduced in 200 ml of methanol, at 3 atmospheres of hydrogen in the presence of 5% Pd/carbon. After removal of the catalyst by filtration, concentration of the filtrate gives 5.3 g of product (3,3-dimethylbutyrylamino)aniline, m.p. 138°-140° C.

Aufarbeitung

  1. customThe resultant solid was collected on
  2. filtrationa filter
  3. dissolutiondissolved in 200 ml of ethyl acetate
  4. additionthe solution was treated with activated charcoal
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aab990405b724fe1b6d04dd0e1b40daa
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578390

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