Phosphorus tribromide → HCID 118324094, compound

HRID 1778270Notes

Reaction equation

HRID 1778270 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]2[C:12]=1[NH:11][CH:10]=[CH:9][C:8]2=O.P(Br)(Br)[Br:19]>CN(C)C=O>[Br:19][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([C:14]([O:16][CH3:17])=[O:15])[CH:6]=2)[N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 118324103HCID 118324103, compound

Product 1

HCID 118324094HCID 118324094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 8-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate (14 g, 60.03 mmol, 1.00 equip), and N,N-dimethylformamide (200 mL). To the resulting mixture was then added PBr3 (17.8 g, 65.76 mmol, 1.10 equip) dropwise with stirring. The resulting solution was stirred for 3 h at 25° C. The reaction was then quenched by the addition of water (1000 mL). The pH value of the solution was adjusted to 8-9 with sodium bicarbonate. The solids were collected by filtration to yield methyl 4-bromo-8-methoxyquinoline-6-carboxylate as a yellow solid. LCMS (ES, m/z) 296 [M+H]+

Workup

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of water (1000 mL)
  4. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-311f51976aaf46a1905158902e8f31c9
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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