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

HRID 1040931ノート

反応式

HRID 1040931 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-803aefa72ee844768ed9a924639303c2
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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