3-Nitropyridin-2-ylamine → 2-Bromo-3-nitropyridine

HRID 2067925Notes

Reaction equation

HRID 2067925 reaction equation
[Br:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.NC1C([N+:16]([O-:18])=[O:17])=CC=CN=1>Br>[Br:1][C:2]1[C:7]([N+:16]([O-:18])=[O:17])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 778873-Nitropyridin-2-ylamine2×HCID 8171022,3-Dibromopyridine

Product 1

HCID 5550542-Bromo-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Bouillon et al in Tetrahedron, 2002, 58, 17, 3323-3328 reported a three-step process for the preparation of 2,3-dibromopyridine from 2-amino-3-nitropyridine. The process involves diazotization of 2-amino-3-nitropyridine followed by addition of CuBr in 47% HBr to obtain 2-bromo-3-nitropyridine. The 2-bromo-3-nitropyridine so obtained is reduced with Fe and acetic acid to 3-amino-2-bromopyridine and subsequent diazotization to give 2,3-dibromopyridine.

Sources & evidence

ORD record
ord-7b0313d5e5e14bca9d9eb20cacab75c0
Source dataset
uspto-grants-2012_10
Patent number
US08293918B2

Reaction notes

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