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

HRID 1040931노트

반응식

HRID 1040931 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-803aefa72ee844768ed9a924639303c2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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