Water → 2-Amino-3-bromo-5-nitropyridine

HRID 256814Notes

Reaction equation

HRID 256814 reaction equation
[Br:1]Br.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1.O>C1COCC1>[NH2:3][C:4]1[C:9]([Br:1])=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 778882-Amino-5-nitropyridine

Product 1

HCID 27344122-Amino-3-bromo-5-nitropyridineYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromine (62.6 mλ; 1.2 mole) was dropwise added to 2-amino-5-nitropyridine (154.1 g; 1.1 mole) in THF (300 mλ) at room temperature. The resulting mixture was stirred for one hour and then poured into water (3 λ). The crystals thus formed were recrystallized from acetonitrile (500 mλ) to give 2-amino-3-bromo-5-nitropyridine (A) (194.4 g; 80%).

Workup

  1. customThe crystals thus formed
  2. customwere recrystallized from acetonitrile (500 mλ)

Sources & evidence

ORD record
ord-26599012638c4f07aecf33ce3718ca2c
Source dataset
uspto-grants-1993_11
Patent number
US05260177

Reaction notes

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