Aniline → 5-BROMO-N-PHENYLNICOTINAMIDE

HRID 1620038Notes

Reaction equation

HRID 1620038 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[Br:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=1)[C:36](O)=[O:37].[Cl-].[NH4+]>C(OCC)(=O)C.CN(C=O)C.O>[Br:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=1)[C:36]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:37]

Participants

9

Reactant 5

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 887075-Bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 42730445-BROMO-N-PHENYLNICOTINAMIDE

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Aniline (99 μl), WSC.HCl (209 mg), and HOBt.H2O (167 mg) were added to a DMF (5 ml) solution containing 5-bromonicotinic acid (200 mg), followed by stirring at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether and hexane were added to the obtained residue, solid matter was collected by filtration, and a white solid of 5-bromo-N-phenylnicotinamide (268 mg) was thus obtained.

Workup

  1. customThe organic layer was collected
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionDiisopropylether and hexane were added to the obtained residue, solid matter
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d3dece159a5e4d76b8760de8b9601b1e
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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