2-(Methoxymethyl)-4-nitroaniline → 2-Methoxymethyl-p-phenylenediamine

HRID 1472976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472976
[CH3:1][O:2][CH2:3][C:4]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:5]=1[NH2:6].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH2:3][C:4]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=1[NH2:6]

Komponenten

5

Edukt 2

HCID 114011432-(Methoxymethyl)-4-nitroanilineHCID 178418361HCID 178418361, Verbindung3×

Produkt 1

HCID 97938592-Methoxymethyl-p-phenylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Into a Parr hydrogenation bottle previously purged with argon, are placed a solution of 2-methoxymethyl-4-nitroaniline (5.0 g, 27.5 mmol) in ethyl acetate (50 mL) and 0.25 g of 10% palladium on carbon. The bottle is mounted on a Parr shaker and hydrogenation is carried out under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. The pressure is carefully monitored for hydrogen uptake and additional hydrogen is introduced to keep the pressure above 50 psig. The hydrogenation is carried out for 3.5 hours after which the catalyst is removed by vacuum filtration. The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration and dried at 60° C. under vacuum. The product yield is 4.5 g. 1H-NMR (500 MHz, DMSO-d6) δ 3.23 (s, 3H), 4.11 (s, 2H), 4.21 (s, 2H), 4.24 (s, 2H), 6.33 (dd, 1H), 6.37 (d, 1H), 6.41 (d, 1H).

Aufarbeitung

  1. customInto a Parr hydrogenation bottle previously purged with argon
  2. additionis introduced
  3. customafter which the catalyst is removed by vacuum filtration
  4. concentrationThe filtrate is concentrated to about 25 mL and toluene (25 mL)
  5. additionis added
  6. customto precipitate the product, which
  7. filtrationis collected by vacuum filtration
  8. customdried at 60° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c8981a6c3f7541b999c172325e305d88
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012691B2

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