Phosphorus tribromide → Ethyl 4-bromo-6-methoxyquinoline-3-carboxylate

HRID 2356319Notes

Reaction equation

HRID 2356319 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1O)=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)=[O:9])[CH3:6]>CN(C=O)C>[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[Br:2])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178469588HCID 178469588, compound

Product 1

HCID 49758155Ethyl 4-bromo-6-methoxyquinoline-3-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

PBr3 (64.5 g, 22.5 mL, 0.239 mole) was added dropwise to a stirred, ice cold suspension of 4-hydroxy-6-methoxy-quinoline-3-carboxylic acid ethyl ester (59 g, 0.239 mole) in DMF (750 mL); the temperature rose to 15-20° C. for 30 min and then dropped to ca. 5° C. (the starting material dissolved fairly quickly and a new solid precipitated out). After 3 hr the solid was collected, washed sequentially with cold DMF, hexane, and water, then was dried at 40° C. in vacuo overnight to give the title compound (41 g, 78%): LC/MS (ES) m/e 310/312 (M+H)+.

Workup

  1. additiondropped to ca. 5° C. (the starting material
  2. dissolutiondissolved fairly quickly
  3. customa new solid precipitated out)
  4. customAfter 3 hr the solid was collected
  5. washwashed sequentially with cold DMF, hexane, and water
  6. customwas dried at 40° C. in vacuo overnight

Sources & evidence

ORD record
ord-232f5d04dce141db8a149e6abbe503e7
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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