2-Methyl-4-nitroaniline → HCID 13325055, Verbindung

HRID 436342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436342
[C:1]([C:6]1[CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]([OH:15])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:16][C:17]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH2:19].P(Cl)(Cl)Cl>C1(C)C(C)=CC=CC=1>[C:1]([C:6]1[CH:14]=[C:10]([C:11]([NH:19][C:18]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:17]=2[CH3:16])=[O:13])[C:9]([OH:15])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 74412-Methyl-4-nitroanilineHCID 24387Phosphorus trichlorideHCID 2687425-tert-amylsalicylic acid

Produkt 1

HCID 13325055HCID 13325055, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 10.4 g of 5-tert-amylsalicylic acid and 7.6 g of 2-methyl-4-nitroaniline in 100 ml of xylene is heated at 70° C and to the mixture is added a solution of 2.6 g of phosphorus trichloride in 10 ml of xylene. The whole mixture is refluxed for two and a half hours. The hot reaction solution is decanted. The supernatant solution is cooled on an ice bath. The crystalline precipitate is collected by filtration. Recrystallization from methanol gives 9.4 g of the title compound as pale yellow crystals, melting at 150°-151° C.

Aufarbeitung

  1. temperatureThe whole mixture is refluxed for two and a half hours
  2. customThe hot reaction solution is decanted
  3. temperatureThe supernatant solution is cooled on an ice bath
  4. filtrationThe crystalline precipitate is collected by filtration
  5. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-d50b71e33c6a4b27a4aea1b073c2c676
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008274

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