Hydrazine hydrate (1:1) → (2-Bromo-4,5-dimethoxy benzoyloxy) hydrazine

HRID 1525790

Reaktionsgleichung

Reaktionsgleichung von HRID 1525790
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[Br:14].O.[NH2:17][NH2:18]>CCO>[Br:14][C:5]1[CH:6]=[C:7]([O:12][CH3:13])[C:8]([O:10][CH3:11])=[CH:9][C:4]=1[C:3]([O:2][NH:17][NH2:18])=[O:15]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 2817399Methyl 2-bromo-4,5-dimethoxybenzoate

Produkt 1

HCID 68294039(2-Bromo-4,5-dimethoxy benzoyloxy) hydrazineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A mixture of 0.960 g (3.48 mmol) of 7, 1.60 g (35 mmol) of hydrazine hydrate (62% hydrazine), and 5 mL of EtOH was refluxed for 15 h. The mixture was cooled to −20° C., vacuum filtered, washed with 50 mL of ice-cold 1:1 EtOH:H2O, and dried to give 0.832 g (87% yield) of (2-bromo-4,5-dimethoxy benzoyloxy)hydrazine (8) as a white, needle-like crystalline solid. The above procedure was repeated on 2.79 g of the starting ester 7 to result in 2.77 g (99% yield) of 8. 1H NMR (200 MHz, CDCl3) δ 6.97 (s, 1H), 6.86 (s, 1H), 3.85 (s, 6H). HRMS Calculated for C9H12O3N2Br 275.0031. found 275.0037.

Aufarbeitung

  1. temperaturewas refluxed for 15 h
  2. filtrationvacuum filtered
  3. washwashed with 50 mL of ice-cold 1:1 EtOH
  4. dry with materialH2O, and dried

Quellen und Nachweise

ORD-Eintrag
ord-dce69c28b2cb4933b48c2f07ef300d8b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085549B2

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