Pyridine → 7-(2-Bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester

HRID 51919

반응식

HRID 51919 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[N:19]2)=[CH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:25]([O:24][C:22]([C:17]1[CH:18]=[N:19][C:20]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([NH:11][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Br:1])[CH:21]=2)=[O:23])[CH3:26]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 235422-Bromobenzoyl chlorideHCID 9877801Ethyl 7-aminoquinoline-3-carboxylate

생성물 1

HCID 698911587-(2-Bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester수율 50%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

A solution of 2-Bromobenzoyl chloride (5.38 g, 24.5 mmol) in 100 ml chloroform was added dropwise at room temperature to a solution of ethyl 7-aminoquinoline-3-carboxylate (2.65 g, 12.25 mmol), 4-N,N-dimethylaminopyridine (150 mg, 1.23 mmol) and pyridine (3.96 ml, 49 mmol) in 100 ml chloroform. The resulting solution was heated under reflux for 4 hr, then cooled to room temperature. The chloroform solution was then washed sequentially with dilute aqueous hydrochloric acid solution, water and brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was chromatographed on silica gel, eluting with 60:40 hexane/ethyl acetate to yield the title product as a solid foam (2.45 g 50% yield).

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 4 hr
  3. washThe chloroform solution was then washed sequentially with dilute aqueous hydrochloric acid solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluting with 60:40 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-515124e287874ebd87ffdaa652a8f319
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713489B2

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