4-Fluoroaniline → 2-bromonicotinamide

HRID 404762Notes

Reaction equation

HRID 404762 reaction equation
[Br:1][C:2]1C=CC(C(O)=O)=C[N:3]=1.F[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=C[CH:13]=1.CC[O:21]C1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>CN(C=O)C>[Br:1][C:2]1[N:3]=[CH:13][CH:12]=[CH:18][C:17]=1[C:15]([NH2:16])=[O:21]

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 2389326-Bromonicotinic acid

Product 1

HCID 8171612-bromonicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromonicotinic acid (5.28 g, 26 mmol) and 4-fluoroaniline (2.90 g, 26 mmol) was dissolved in anhydrous DMF (30 mL). EEDQ was added, and the reaction was allowed to progress overnight at room temperature. The solvent was removed by rotary evaporation, and the crude material was dissolved in hot EtOAc (50 mL). Upon cooling, the product crystallized from the solution. The product was filtered, washed with cold EtOAc to yield 3.29 g (43%) as a white solid. ESI-MS m/z=294.9, 296.8 [M+H]+.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe crude material was dissolved in hot EtOAc (50 mL)
  3. temperatureUpon cooling
  4. customthe product crystallized from the solution
  5. filtrationThe product was filtered
  6. washwashed with cold EtOAc
  7. customto yield 3.29 g (43%) as a white solid

Sources & evidence

ORD record
ord-005a8875b4b74a8ba0aa5588d3f0ed11
Source dataset
uspto-grants-2014_06
Patent number
US08748623B2

Reaction notes

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