4-Fluoroaniline → 2-bromonicotinamide

HRID 875161Notes

Reaction equation

HRID 875161 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-545ea378a88a45f7be48a088cb7b3f9c
Source dataset
uspto-grants-2015_03
Patent number
US08981106B2

Reaction notes

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