Methyl 4-aminobenzoate → Methyl 4-hydrazinylbenzoate

HRID 509718

Reaktionsgleichung

Reaktionsgleichung von HRID 509718
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[N:12]([O-])=O.[Na+].[Sn](Cl)(Cl)(Cl)Cl>Cl.O>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[NH2:12]

Komponenten

6

Edukt 3

HCID 12082Methyl 4-aminobenzoateHCID 24287Tin tetrachlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 408928Methyl 4-hydrazinylbenzoateAusbeute 112,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl 4-aminobenzoate (5.0 g, 0.0331 moles) was taken up in conc. HCl (50 mL) and cooled to 0° C. Sodium nitrite (2.5 g, 0.0331 moles) solution in water was added at 0° C. over 30 minutes and stirred at RT for 90 min. Tin chloride (19.40 g, 0.0927 moles) in HCl (100 mL) was added drop wise at 0° C. and stirred at RT for 2 hr. The reaction was filtered and the solid obtained was washed with diethyl ether and dried on a rotary evaporator to give 6.2 g, 92.53% yield of Methyl 4-hydrazinylbenzoate as a white solid.

Aufarbeitung

  1. stirringstirred at RT for 2 hr
  2. filtrationThe reaction was filtered
  3. customthe solid obtained
  4. washwas washed with diethyl ether
  5. customdried on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-d718d8b6af2e4695a0699b705791e9c1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096591B2

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