Phosphorus tribromide → HCID 68576825, compound

HRID 638991Notes

Reaction equation

HRID 638991 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=O.P(Br)(Br)[Br:21].C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[Br:21][C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=2)[N:10]=[CH:9][C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 68577453HCID 68577453, compound

Product 1

HCID 68576825HCID 68576825, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 8-fluoro-6-(methoxy)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (12 g, 45 mmol) in DMF (56 ml) was added dropwise phosphorus tribromide (4.5 ml, 47 mmol) over fifteen minutes (slightly exothermic). The reaction was held at 0° C., with an ice bath, for one hour and allowed to warm to room temperature then stirred for a further 2 hours. The mixture was then diluted with water (400 mL). A solution of sodium bicarbonate was added to reach pH 7. The reaction mixture was stirred for one hour at 0° C. then filtered. The precipitate was washed with water and dried in vacuo to afford the product as a yellow solid (12.2 g, 82%).

Workup

  1. stirringThe reaction mixture was stirred for one hour at 0° C.
  2. filtrationthen filtered
  3. washThe precipitate was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7dd7bde52d11484fb15bcf9fea81d093
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

Loading…