N-bromobutanimide → 4-Quinolinecarboxylic acid, 3-(bromomethyl)-2-phenyl-, methyl ester

HRID 1837381노트

반응식

HRID 1837381 반응식
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH3:21])=[O:4].[Br:22]N1C(=O)CCC1=O>CC#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:21][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][C:9]2[C:14]([C:5]=1[C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=[CH:11][CH:10]=2

참가 물질

5

반응물 2

HCID 67184N-bromobutanimide2회HCID 230804Methyl 3-methyl-2-phenylquinoline-4-carboxylate

생성물 1

HCID 104984484-Quinolinecarboxylic acid, 3-(bromomethyl)-2-phenyl-, methyl ester수율 203.5%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매2회HCID 6342Acetonitrile용매

실험 절차

10 g (36 mmol) of 3-methyl-2-phenylquinoline-4-carboxylic acid methyl ester (compound of Description A) were dissolved in 500 ml of CH3CN; 13 g (72 mmol) of N-bromosuccinimide were added and the reaction mixture was heated to reflux. After adding 1 g (4.1 mmol) of dibenzoylperoxide, the reaction was refluxed for 24 h; then additional 4 g (22.5 mmol) of N-bromosuccinimide and 0.5 g (2.0 mmol) of dibenzoylperoxide were added and the reaction was refluxed for 4 h. The solvent was evaporated in vacuo to dryness to yield 26.1 g of crude methyl 3-bromomethyl-2-phenylquinoline-4-carboxylate (theorical amount, 12.8 g) which was used in the following reaction without further purification.

후처리

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturethe reaction was refluxed for 24 h
  3. temperaturethe reaction was refluxed for 4 h
  4. customThe solvent was evaporated in vacuo to dryness

출처 및 근거

ORD 기록
ord-4b8c6590f6384f8fb2592dcbe6901e7a
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780875B2

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