Water → 4-ethyl-6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234897노트

반응식

HRID 234897 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]([CH3:14])[C:11](=[O:15])[NH:10][C:9]=2[CH:16]=1)=[O:4].[H-].[Na+].[CH2:19](I)[CH3:20].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:10]1[C:9]2[CH:16]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[CH:7][C:8]=2[O:13][CH:12]([CH3:14])[C:11]1=[O:15])[CH3:20]

참가 물질

7

반응물 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10656590methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

생성물 1

HCID 105625644-ethyl-6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine수율 80.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (2.2 g) in dimethylformamide (20 ml) were added 60% sodium hydride (in oil) (0.5 g) and ethyl iodide (1.8 g) and the mixture was stirred at room temperature for a day. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure and the resulting residue was subjected to purification by column chromatography using ethyl acetate/hexane [1:1 (v/v)] to give 4-ethyl-6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (2.0 g).

후처리

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was subjected to purification by column chromatography

출처 및 근거

ORD 기록
ord-91f57d15239046dabba8517a557f58e9
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597820

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