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

HRID 1687238Notes

Reaction equation

HRID 1687238 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-62afaeb40310404cbe312a67c46cd22c
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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