Propionyl chloride → N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamide

HRID 1784844Notes

Reaction equation

HRID 1784844 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.[C:26](Cl)(=[O:29])[CH2:27][CH3:28].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:26](=[O:29])[CH2:27][CH3:28])[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=1

Participants

6

Reactant 4

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 50994432(3-Amino-5-bromo-phenyl)-pyridin-3-yl-methanone

Product 1

HCID 68844539N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamide

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To 0.20 g of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 10 mL of dichloroethane was added 0.25 mL of diisopropylethylamine and 0.065 mL of propionyl chloride. The reaction was stirred 1 h at ambient temperature, then poured into saturated aqueous sodium bicarbonate. The phases were separated and the aqueous phase was washed once with methylene chloride, dried over sodium sulfate, filtered and concentrated to give 0.24 g (quantitative yield) of N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamide.

Workup

  1. customThe phases were separated
  2. washthe aqueous phase was washed once with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c80f051e3b5148c9a0d49ede2623aee0
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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