Pyridinium hydrobromide → 4-Bromo-6-hydroxynicotinonitrile

HRID 56720Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([O:8]C)[N:5]=[CH:4][C:3]=1[C:10]#[N:11].[BrH:12].[NH+]1C=CC=CC=1>>[Br:12][C:2]1[C:3]([C:10]#[N:11])=[CH:4][NH:5][C:6](=[O:8])[CH:7]=1

Participants

Reactant 2

HCID 21226041Pyridinium hydrobromide

HCID 1176054124-Iodo-6-methoxynicotinonitrile

Product 1

HCID 1176057064-Bromo-6-hydroxynicotinonitrile

Procedure

4.5 g (purity 90%, 15.6 mmol) of 4-iodo-6-methoxypyridin-3-carbonitrile and 20 eq. of pyridinium hydrobromide were reacted according to General Method 3A. After aqueous work-up, the crude product was reacted further without further purification. Yield: 1.99 g (purity 77%, 49% of theory) of the title compound as a mixture with 11% of the analogous iodine compound.

Sources & evidence

ORD record: ord-91a70cd59bc34a54b8be91e67d522b59
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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