Dimethylformamide → 4-methyl-8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one

HRID 1687238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1687238
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[NH:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:18]N(C=O)C>>[CH3:18][N:9]1[C:8](=[O:13])[C:7]2[CH:14]=[CH:15][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[O:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 578537818-nitro-3,4-dihydro-2H-1,4-benzoxazepin-5-one

Produkt 1

HCID 672633784-methyl-8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-oneAusbeute 77 %

Versuchsvorschrift

A solution of 8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.25 g, 0.0012 mol) in DMF (8 mL) at 5° C. under nitrogen, was treated with sodium hydride (0.058 g, 0.0015 mol). After stirring 15 hrs. at room temperature, the reaction was evaporated. The residue was treated with ethyl acetate and 1N HCl (pH 5), separated, washed, dried (MgSO4) to give 4-methyl-8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.2 g, 77%) as a tan solid. MP: 130-2° C.; 1H-NMR (DMSO-d6) δ 7.90-8 (d, 1H), 7.88 (d, 1H), 7.80 (d, 1H), 4.46-8 (m, 2H), 3.56-9 (m, 2H), 3.11 (s, 3H); LC/MS (ESI+): 223 (M+H).

Aufarbeitung

  1. customat room temperature, the reaction was evaporated
  2. additionThe residue was treated with ethyl acetate and 1N HCl (pH 5)
  3. customseparated
  4. washwashed
  5. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-62afaeb40310404cbe312a67c46cd22c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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