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

HRID 1837381Notes

Reaction equation

HRID 1837381 reaction equation
[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

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 230804Methyl 3-methyl-2-phenylquinoline-4-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4b8c6590f6384f8fb2592dcbe6901e7a
Source dataset
uspto-grants-2004_08
Patent number
US06780875B2

Reaction notes

Loading…