2-Isopropylaniline → 2-Isopropylphenylhydrazine

HRID 1438913

Reaktionsgleichung

Reaktionsgleichung von HRID 1438913
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[N:11]([O-])=O.[Na+]>O.Cl>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][NH2:11])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 125612-IsopropylanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 7045932-Isopropylphenylhydrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel3×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of the substituted aniline, 2-isopropylaniline (27g, 0.2 mole), concentrated hydrochloric acid (150 ml) and water (160 ml) is stirred mechanically for 30 minutes at room temperature. After cooling to 0° C, the mixture is diazotized by adding dropwise a solution of sodium nitrite (14 g, 0.203 mole) in water (140 ml) over a period of 20 minutes. Stirring is continued for an additional one hour at 0° C. The diazo solution is reduced by adding dropwise a solution of stannous chloride dihydrate (112 g, 0.497 mole) in concentrated hydrochloric acid (90 ml) over a period of 30 minutes at -10° C to -15° C. The reaction mixture is stirred for an additional 1.5 hour at -10° C to -15° C. The precipitate is collected by filtration to give the hydrochloric acid addition salt of the title compound. The salt is purified further by dissolving it in ethanol, concentrating the solution and adding a saturated solution of hydrochloric acid in either to give the hydrochloride salt with mp 206° - 210° C.

Aufarbeitung

  1. temperatureAfter cooling to 0° C
  2. stirringStirring
  3. waitis continued for an additional one hour at 0° C
  4. stirringThe reaction mixture is stirred for an additional 1.5 hour at -10° C to -15° C
  5. filtrationThe precipitate is collected by filtration
  6. customto give

Quellen und Nachweise

ORD-Eintrag
ord-8a522181e1da46f39325a23b4414daad
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04057559

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