4-(p-Tolyloxy)aniline → HCID 68512931, Verbindung

HRID 1716294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716294
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]1([CH3:26])[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:15]3[CH:16]=[CH:17][C:12]([CH3:26])=[CH:13][CH:14]=3)=[CH:24][CH:23]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 945194-(p-Tolyloxy)anilineHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 4311764Sodium borohydride2×

Produkt 1

HCID 68512931HCID 68512931, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5-bromo-2-methoxy-pyridine-3-carbaldehyde (0.87 g, 4.03 mmol) in dry MeOH (15 mL) was treated with 4-p-tolyloxy-phenylamine (0.88 g, 4.43 mmol) and reflux for 2.5 h. The solution was cooled to 0° C. and treated slowly with NaBH4 (0.38 g, 10.1 mmol). The reaction stirred at room temperature overnight. Additional NaBH4 (0.38 g, 10.1 mmol) was added and the reaction was continued stirring for additional 6 h. The solvent was removed and the residue was partitioned between CH2Cl2 (20 mL) and water (10 mL). The organic portion was brought to the usual work-up to give a crude material. The product was yielded after chromatography purification (silica gel, 25% EtOAc/hexanes). MS (EI) 399, 401 (M+H)+.

Aufarbeitung

  1. temperaturereflux for 2.5 h
  2. stirringthe reaction was continued stirring for additional 6 h
  3. customThe solvent was removed
  4. customthe residue was partitioned between CH2Cl2 (20 mL) and water (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6a3c5efd0a644e5d901c45ad6e36b609
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803793B2

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