Hydrochloric Acid → 3-Bromo-2-benzoylamino-5-nitropyridine

HRID 256815Notes

Reaction equation

HRID 256815 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(#N)C>[Br:14][C:13]1[C:8]([NH:7][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 27344122-Amino-3-bromo-5-nitropyridine

Product 1

HCID 197840833-Bromo-2-benzoylamino-5-nitropyridineYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20 mλ of pyridine was added to 2-amino-3-bromo-5-nitropyridine (A) (21.8 g; 0.1 mole) in 300 ,λ of acetonitrile at room temperature in a stream of nitrogen followed by addition of benzoylchloride (24.4 g; 0.2 mole) and agitation for 3 hours. Then dilute hydrochloric acid (0.1N) was added to the resulting mixture. After extraction with ethyl acetate, the resulting ethyl acetate solution was dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure. The residue was recrystallized from methanol to give 3-bromo-2-benzoylamino-5-nitropyridine (B) (28.7 g; 89%).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe resulting ethyl acetate solution was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under a reduced pressure
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-94847534671745609f1c58357504e4c3
Source dataset
uspto-grants-1993_11
Patent number
US05260177

Reaction notes

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