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

HRID 37125

反応式

HRID 37125 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2cdbbf7a2ff64de481fa31b88634e9f2
出典データセット
uspto-grants-1995_05
特許番号
US05420126

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