Sodium Hydroxide → 1-Acetyl-8-nitro-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one

HRID 1687568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1687568
[C:1]([N:4]1[CH2:11][CH2:10][C:9](=[O:12])[NH:8][CH2:7][C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]1=2)(=[O:3])[CH3:2].[OH-].[Na+].[N+:19]([O-])([OH:21])=[O:20].OS(O)(=O)=O>>[C:1]([N:4]1[CH2:11][CH2:10][C:9](=[O:12])[NH:8][CH2:7][C:6]2[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:5]1=2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 672641101-Acetyl-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-oneHCID 71777668Sulfuric acid, mixt. with nitric acid

Produkt 1

HCID 672645601-Acetyl-8-nitro-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Acetyl-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one (1.05 g, 4.82 mmol) was added to a 1/1 mixture of HNO3/H2SO4 (20 ml) at 0° C. The resulting solution was stirred at 0° C. for 3 h and allowed to warm to rt over 16 h. The reaction mixture was poured onto ice and neutralized with NaOH. The resulting ppt was filtered and washed with H2O to afford title compound as a pale orange solid. (600 mg, 47%). mp 253-256° C.; LCMS: m/z=264.25 (M+H+), HPLC (95% purity); 1H NMR (400 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.24 (d, J=8.8 Hz, 1H), 7.79 (m, 1H), 7.69 (d, J=8.6 Hz, 1H). 4.65 (m, 1H), 4.38 (m, 1H), 4.11 (m, 1H), 2.96 (m, 1H), 2.61 (m, 1H), 2.38 (m, 1H), 1.73 (s, 3H).

Aufarbeitung

  1. temperatureto warm to rt over 16 h
  2. filtrationThe resulting ppt was filtered
  3. washwashed with H2O

Quellen und Nachweise

ORD-Eintrag
ord-e903579484004964967cb8ee4bf3640f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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