Phosphorus tribromide → Methyl 4,8-dibromoquinoline-6-carboxylate

HRID 1778264Notes

Reaction equation

HRID 1778264 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=O.P(Br)(Br)[Br:18].C([O-])(O)=O.[Na+]>CN(C=O)C.O>[Br:18][C:7]1[C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 118324114Methyl 8-bromo-4-oxo-1,4-dihydroquinoline-6-carboxylate

Product 1

HCID 118324078Methyl 4,8-dibromoquinoline-6-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of methyl 8-bromo-4-oxo-1,4-dihydroquinoline-6-carboxylate (272 mg, 0.964 mmol) in DMF (5 mL) at room temperature was added slowly phosphorous tribromide (0.1 mL, 1.06 mmol). The resulting mixture was stirred under argon for 30 min. The reaction mixture was made basic by the addition of solid NaHCO3 until the pH was greater than 10, and then the reaction mixture was diluted with water and the solid collected by filtration. The product was washed with several portion of water and dried to yield methyl 4,8-dibromoquinoline-6-carboxylate. (M+H)+: 344, 346, 348.

Workup

  1. filtrationthe solid collected by filtration
  2. washThe product was washed with several portion of water
  3. customdried

Sources & evidence

ORD record
ord-9b062c4591004164a848fe117b881ed2
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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