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

HRID 841782Notes

Reaction equation

HRID 841782 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b33fe7d925734fe9ab79b9b4842a1f19
Source dataset
uspto-grants-2002_04
Patent number
US06369075B1

Reaction notes

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