Sodium Iodide → 6-Bromo-1,2,3,4-tetrahydroquinoxalin-2-one

HRID 44187노트

반응식

HRID 44187 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:13])[CH2:11]Cl.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Br:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[NH:9][C:10](=[O:13])[CH2:11][NH:1]2

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 66911433N-(2-Amino-4-bromophenyl)-2-chloroacetamide

생성물 1

HCID 669113076-Bromo-1,2,3,4-tetrahydroquinoxalin-2-one수율 34.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of N-(2-amino-4-bromophenyl)-2-chloroacetamide (4.5 g, 17.0 mmol), sodium iodide (101 mg, 2.0 mmol) and sodium carbonate (3.6 g, 33.8 mmol) in 300 ml acetonitrile was refluxed overnight under an atmosphere of nitrogen. Then the acetonitrile was removed under vacuum. The resulting solid was suspended in 150 ml water acidified to pH 5-6 with 1 N HCl. Extraction with ethyl acetate, washing of the combined organic layers with brine, drying over MgSO4, removing the solvent under reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1.5/1) yielded 6-bromo-3,4-dihydroquinoxalin-2(1H)-one (1.3 g, 5.8 mmol, 34%) as yellow solid.

후처리

  1. temperaturewas refluxed overnight under an atmosphere of nitrogen
  2. customThen the acetonitrile was removed under vacuum
  3. extractionExtraction with ethyl acetate
  4. washwashing of the combined organic layers with brine
  5. dry with materialdrying over MgSO4
  6. customremoving the solvent
  7. customunder reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1.5/1)

출처 및 근거

ORD 기록
ord-42eee9138f1c4f8c95f371ff90bc6edb
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541404B2

반응 노트

불러오는 중…