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

HRID 1040931Notes

Reaction equation

HRID 1040931 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-803aefa72ee844768ed9a924639303c2
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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