Ammonia → 5-Bromonicotinamide

HRID 902572Notes

Reaction equation

HRID 902572 reaction equation
[NH3:1].[Br:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:11]=1)[C:8](Cl)=[O:9]>O1CCCC1.[Cl-].[Na+].O>[Br:2][C:3]1[CH:11]=[C:7]([C:8]([NH2:1])=[O:9])[CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 27812235-Bromonicotinoyl chloride

Product 1

HCID 18085-Bromonicotinamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In an amount of 555 mg of 5-bromonicotinoyl chloride was dissolved in 5.5 ml of tetrahydrofuran, added with 768 μl of 28% aqueous ammonia under ice cooling, stirred for 40 minutes, then warmed to room temperature, and further stirred at room temperature for 20 minutes. The reaction system was added with 15% brine, and extracted with tetrahydrofuran, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. Then, the filtrate was concentrated under reduced pressure until about half amount of crystals were deposited, and added with ethyl acetate until the deposition of crystals was terminated, and the crystals were taken by filtration to obtain 374 mg of the title compound.

Workup

  1. stirringfurther stirred at room temperature for 20 minutes
  2. extractionextracted with tetrahydrofuran
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThen, the filtrate was concentrated under reduced pressure until about half amount of crystals
  6. additionadded with ethyl acetate until the deposition of crystals
  7. customwas terminated
  8. filtrationthe crystals were taken by filtration

Sources & evidence

ORD record
ord-139507ae54984d8bb86816533ddb311d
Source dataset
uspto-grants-2008_04
Patent number
US07365174B2

Reaction notes

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