Sodium hydride → 2-(3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-4-yl)pyridine N-oxide

HRID 37125

반응식

HRID 37125 반응식
[H-].[Na+].[CH3:3][C:4]1([CH3:17])[CH2:9][NH:8][C:7]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:6]=2[O:5]1.Cl.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N+:21]=1[O-:26]>CN(C)C=O>[CH3:3][C:4]1([CH3:17])[CH2:9][N:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N+:21]=2[O-:26])[C:7]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:6]=2[O:5]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27240442-Bromopyridine 1-oxide hydrochlorideHCID 104885702,2-Dimethyl-7-nitro-3,4-dihydro-2H-benzo[B][1,4]oxazine

생성물 1

HCID 105661912-(3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-4-yl)pyridine N-oxide수율 23.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

In 14 ml of N,N-dimethylformamide was suspended 0.38 g of sodium hydride (60% in oil) followed by addition of 1.00 g of 3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazine. Then, 1.01 g of 2-bromopyridine N-oxide hydrochloride was added with ice-cooling and the mixture was stirred at 70° C. for 16 hours. The reaction mixture was poured in ice-water and extracted with ethyl acetate. The organic layer was washed with aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to silica gel column chromatography and elution was carried out with chloroform-acetone (3:1) to give 0.34 g of 2-(3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-4-yl)pyridine N-oxide as oil. Then, a solution of hydrochloric acid in ethanol (prepared from 1 ml of concentrated hydrochloric acid and 5 ml of ethanol) was added thereto and the solvent was distilled off. The resulting residue wad recrystallized from acetone to give 182 mg of 2-(3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-4-yl)pyridine N-oxide hydrochloride.

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. washThe residue was subjected to silica gel column chromatography and elution

출처 및 근거

ORD 기록
ord-2cdbbf7a2ff64de481fa31b88634e9f2
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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