N-bromobutanimide → [(8-Bromo-1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl Ester

HRID 48241노트

반응식

HRID 48241 반응식
[CH2:1]([O:3][C:4](=[O:21])[C:5]([NH:7][C:8]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][NH:13]2)=[O:6])[CH3:2].[Br:22]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:21])[C:5]([NH:7][C:8]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([Br:22])=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][NH:13]2)=[O:6])[CH3:2]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 10334564[(1,2,3,4-Tetrahydro-6-nitro-5-quinolinyl)amino]oxo-acetic Acid Ethyl Ester

생성물 1

HCID 10474405[(8-Bromo-1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl Ester수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of the product from Example 87 (0.15 g, 0.5 mmol) and N-bromosuccinimide (0.23 g, 1 mmol) in 2 mL dimethylformamide was stirred at room temperature for 18 hours. The solution was poured onto methylene chloride/water and separated and the water layer back extracted with methylene chloride. The combined organic layers were washed with water, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (4:1 to 1:1 heptane:ethyl acetate as eluant) to give the title compound (0.15 g, 81% yield).

후처리

  1. additionThe solution was poured onto methylene chloride/water
  2. customseparated
  3. extractionthe water layer back extracted with methylene chloride
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (4:1 to 1:1 heptane:ethyl acetate as eluant)

출처 및 근거

ORD 기록
ord-4371e4c6c5364e52a692bc88fa9d0ae1
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703391B2

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