N-bromobutanimide → 5-Bromo-8-(2,6-dichlorobenzoylamino)-3-methylquinoline

HRID 613488Notes

Reaction equation

HRID 613488 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH3:17])=[CH:12]2)=[O:5].[Br:23]N1C(=O)CCC1=O.N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC(OC)(C)C)C#N>ClCCl.C(OCC)(=O)C>[Br:23][C:10]1[CH:9]=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:2]=2[Cl:1])=[C:16]2[C:11]=1[CH:12]=[C:13]([CH3:17])[CH:14]=[N:15]2

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 195927078-(2,6-Dichlorobenzoylamino)-3-methylquinoline

Product 1

HCID 195924715-Bromo-8-(2,6-dichlorobenzoylamino)-3-methylquinolineYield 17.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-3-methylquinoline (250 mg), N-bromosuccinimide (175 mg) and 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) (23.3 mg) in dichloromethane was refluxed for 2 hours. After cooling, the mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane) to give 5-bromo-8-(2,6-dichlorobenzoylamino)-3-methylquinoline (54.2 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. washwashed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-f2def598310d4f4390e66d27684459e7
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…