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

HRID 44187ノート

反応式

HRID 44187 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-42eee9138f1c4f8c95f371ff90bc6edb
出典データセット
uspto-grants-2013_09
特許番号
US08541404B2

反応ノート

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