3-Methoxyphenylhydrazine hydrochloride → (3-Methoxyphenyl)hydrazine

HRID 333846

Reaktionsgleichung

Reaktionsgleichung von HRID 333846
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:10][NH2:11])[CH:7]=[CH:8][CH:9]=1>[OH-].[Na+]>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:10][NH2:11])[CH:7]=[CH:8][CH:9]=1

Komponenten

3

Edukt 1

HCID 27239403-Methoxyphenylhydrazine hydrochloride

Produkt 1

HCID 423605(3-Methoxyphenyl)hydrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

3-Methoxyphenylhydrazine hydrochloride (1 g) was suspended in 1M aqueous NaOH solution and extracted with ether. The organic phase was dried (MgSO4), filtered and concentrated to dryness to give 3-methoxyphenylhydrazine. 2,5-Dibromobenzaldehyde (1 g) and N-methylpyrrolidone (3.7 ml) were added and the mixture was heated under microwave conditions to 160° C. for 10 min. K2CO3 (1.015 g), CuI (36 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (53 mg) were added and the mixture was heated under microwave conditions to 160° C. for 40 min. CuI (18 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (26 mg) were added and the mixture was heated under microwave conditions to 160° C. for 20 min. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography (SiO2, CH2Cl2/MeOH 100:0=>95:5) to give the title compound (659 mg) as a yellow oil. MS (m/e)=303.0 [M+H+].

Aufarbeitung

  1. extractionextracted with ether
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d875e1bf69bd4a1495496b99f0e59c92
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883786B2

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