Acetic Acid → HCID 10829879, Verbindung

HRID 442668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442668
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([C:15](=O)[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[C:6]([CH2:10][C:11](OC)=[O:12])[CH:7]=2)[O:2]1.O.[NH2:27][NH2:28].C(O)(=O)C>C(O)C>[CH2:1]1[O:2][C:3]2=[CH:4][C:5]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=4)=[N:28][NH:27][C:11](=[O:12])[CH2:10][C:6]=3[CH:7]=[C:8]2[O:9]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 404213Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetate

Produkt 1

HCID 10829879HCID 10829879, VerbindungAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl 4,5-methylenedioxy-2-(4-nitrobenzoyl)phenylacetate (90 mg, 0.26 mmol), hydrazine hydrate (50 μL, 0.88 mmol), and acetic acid (40 μL) in ethanol (15 mL) was refluxed for 4 days. A yellow solid precipitated out from the solution. After cooling, the solvent was removed via pipette and the solid was washed with EtOAc (twice) and hexane, dried in vacuo to provide the title compound (40 mg, 47%), mp: 293°-295° C. 1H NMR (DMSO-d6) 11.2 (s, 1H), 8.31(d, 2H, J=8.8), 7.79 (d, 2H, J=8.8), 7.13 (s, 1H), 6.65 (s, 1H), 6.12 (s, 2H), 3.45 (s, 2H). Anal. Calcd. for C16H11N3O5 : C, 59.08; H, 3.41; N, 12.92. Found: C, 59.05; H, 3.43; N, 2.83.

Aufarbeitung

  1. customA yellow solid precipitated out from the solution
  2. temperatureAfter cooling
  3. customthe solvent was removed via pipette
  4. washthe solid was washed with EtOAc (twice) and hexane
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c9d4305bf88e4e86b8568995907d82c6
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

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