Hydrazinium chloride → HCID 58307451, Verbindung

HRID 222790

Reaktionsgleichung

Reaktionsgleichung von HRID 222790
[CH3:1][C:2]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:13])O[C:4](=[O:5])[CH:3]=1.Cl.[NH2:15][NH2:16]>C(O)C>[CH3:12][O:11][C:9]([C:8]1[C:2]([CH3:1])=[CH:3][C:4](=[O:5])[N:15]([NH2:16])[C:7]=1[CH3:13])=[O:10]

Komponenten

4

Edukt 2

HCID 115031Hydrazinium chlorideHCID 1704852H-Pyran-5-carboxylic acid, 4,6-dimethyl-2-oxo-, methyl ester

Produkt 1

HCID 58307451HCID 58307451, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of methyl isodehydroacetate (24.0 g, 132 mmol) and hydrazine monohydrochloride (9.6 g, 140 mmol) in ethanol (30 mL) was heated under microwave irradiation at 160° C. for 2 hours. It was filtered and the obtained solution was evaporated. The oil was partitioned between sat. aq. Na2CO3 and ethyl acetate (3×250 mL). The combined organic solution was washed with brine, dried (Na2SO4) and evaporated. The title product was purified by flash chromatography (yield 2.8 g, 10%). LC-MS (m/z) 197.0 (MH+); tR=0.57 (method C). 1H NMR (600 MHz, CDCl3): 2.20 (s, 3H, Me), 2.52 (s, 3H, Me), 3.88 (s, 3H, OMe), 5.16 (s, 2H, NH2), 6.35 (s, 1H, C5-H).

Aufarbeitung

  1. filtrationIt was filtered
  2. customthe obtained solution was evaporated
  3. customThe oil was partitioned between sat. aq. Na2CO3 and ethyl acetate (3×250 mL)
  4. washThe combined organic solution was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe title product was purified by flash chromatography (yield 2.8 g, 10%)

Quellen und Nachweise

ORD-Eintrag
ord-3bd340761fa441a3afbe1e7e93423670
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207347B2

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