Acetic Acid → Acetamide, N-[10-(1,3-benzodioxol-5-yl)-7,9-dihydro-7,9-dioxo-8H-1,3-benzodioxolo[4,5-f]isoindol-8-yl]-

HRID 2354599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354599
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]4[C:25](=[O:26])[O:24][C:23](=O)[C:12]=4[CH:13]=[C:14]4[C:22]=3[C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=[CH:15]4)=[CH:9][C:4]=2[O:3][CH2:2]1.O.[NH2:29][NH2:30].[C:31]([OH:34])(=O)[CH3:32]>>[O:21]1[C:17]2[CH:16]=[CH:15][C:14]([C:13]3[C:9]4[C:8](=[CH:7][CH:6]=[C:5]5[O:1][CH2:2][O:3][C:4]5=4)[CH:10]=[C:11]4[C:25](=[O:26])[N:29]([NH:30][C:31](=[O:34])[CH3:32])[C:23](=[O:24])[C:12]=34)=[CH:22][C:18]=2[O:19][CH2:20]1

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 527377710-Benzo[1,3]dioxol-5-yl-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione

Produkt 1

HCID 5273798Acetamide, N-[10-(1,3-benzodioxol-5-yl)-7,9-dihydro-7,9-dioxo-8H-1,3-benzodioxolo[4,5-f]isoindol-8-yl]-Ausbeute 86 %

Versuchsvorschrift

A solution of anhydride 1 (145 mg, 0.4 mmol) in glacial acetic acid (10 mL) was refluxed with hydrazine hydrate (0.023 mL, 0.48 mmol) for 24 h under nitrogen and then poured, after cooling, into ice water. The resulting precipitate was filtered and dried under reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (30:1 to 20:1, v/v) to give 25 (143 mg, 86%) as a yellow solid. mp 281-283° C.; 1H NMR (CDCl3) δ 8.34 (s, 1H, H4), 7.69 (d, 1H, H5, J=8.7 Hz), 7.46 (s, 1H, NHAc), 7.38 (d, 1H, H6, J=8.7 Hz), 6.84-6.87 (m, 3H, H2′+H5′+H6′), 6.06 (AB, 2H, 3′,4′-OCH2O—, Δδ=16.5 Hz, J=1.5 Hz), 5.98 (AB, 2H, 7,8-OCH2O—, Δδ=5.4 Hz, J=1.2 Hz), 2.17 (s, 3H, NHCOCH3); MS (EI) m/z 418 [M]+.

Aufarbeitung

  1. additionpoured
  2. filtrationThe resulting precipitate was filtered
  3. customdried under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9982b5b4fa1d45f6b2d0c2467f1f04fb
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754718B2

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