4-Methyl-2-nitroaniline → (4-Benzyloxy-phenyl)-(4-methyl-2-nitro-phenyl)-amine

HRID 607243

Reaktionsgleichung

Reaktionsgleichung von HRID 607243
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC1C=CC=CC=1C>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([CH3:1])=[CH:3][C:4]=2[N+:9]([O-:11])=[O:10])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 69784-Methyl-2-nitroanilineHCID 11430Potassium CarbonateHCID 1388351-Bromo-4-phenylmethoxybenzene

Produkt 1

HCID 66808397(4-Benzyloxy-phenyl)-(4-methyl-2-nitro-phenyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 4-methyl-2-nitroaniline (1.006 g, 6.612 mmol), 4-benzyloxybromobenzene (5.794 g, 22.02 mmol), cuprous iodide (62.9 mg, 0.3306 mmol), potassium carbonate (0.914 g, 6.612 mmol) and anhydrous o-xylene (18 mL) was heated at 150° for 24 hours. Added additional cuprous iodide (30 mg) and heated an additional 6 hours at 160°. The reaction was cooled to room temperature and the solvent removed by rotary evaporation under vacuum. The residue was purified by silica gel flash chromatography using 1:1 methylene chloride/hexanes as eluent to afford the title compound as a red oil which slowly crystallized (1.23 g, 56%).

Aufarbeitung

  1. temperaturewas heated at 150° for 24 hours
  2. temperatureheated an additional 6 hours at 160°
  3. customthe solvent removed by rotary evaporation under vacuum
  4. customThe residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5a0fae2dbaef4e53adb89bd0f05912eb
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915411B2

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