4-Methyl-2-nitro-1-(1-propen-2-yl)benzene → 2-Isopropyl-5-methylaniline

HRID 62040

Reaktionsgleichung

Reaktionsgleichung von HRID 62040
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[CH2:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1>[Pd].C(OCC)(=O)C>[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[NH2:11])([CH3:10])[CH3:9]

Komponenten

4

Edukt 1

HCID 897388014-Methyl-2-nitro-1-(1-propen-2-yl)benzene

Produkt 1

HCID 205638272-Isopropyl-5-methylaniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (0.986 g, 5.56 mmol) in a 100 mL round-bottomed flask equipped with a stir bar was added ethyl acetate (55.6 mL) and palladium on carbon (1.18 g, 0.556 mmol). The reaction was evacuated and backfilled with hydrogen (balloon). The reaction was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a pad of Celite® and concentrated providing the title compound as a clear and colorless oil (0.788 g, 95%): IR (thin film) 3464 (m), 3372 (m), 3011 (m), 2959 (s), 2869 (m), 1621 (m), 1575 (m), 1509 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=7.8 Hz, 1H), 6.61 (dd, J=7.8, 1.7 Hz, 1H), 6.54-6.50 (m, 1H), 3.59 (bs, 2H), 2.87 (hept, J=6.8 Hz, 1H), 2.24 (s, 3H), 1.24 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 143.14, 136.16, 129.82, 125.33, 119.79, 116.55, 99.97, 27.36, 22.41, 20.96.

Aufarbeitung

  1. customThe reaction was evacuated
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a7b10ddd258843ada25dc2104feb89ae
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

Verknüpfte Notizen

Wird geladen…