Hydrogen Bromide → 2-Cyano-4-hydroxypyridine

HRID 1828425Notes

Reaction equation

HRID 1828425 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=1.Br>>[OH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 134151564-Methoxypyridine-2-carbonitrile

Product 1

HCID 1785102572-Cyano-4-hydroxypyridineYield 301.8%

Conditions

Temperature
130 °C

Procedure

4-Methoxy-2-pyridinecarbonitrile (544 mg, 4.055 mmol) was added with 47% hydrobromic acid (6 ml) and refluxed by heating at 130° C. The reaction solution was stirred for 22 hours, returned to room temperature, and then concentrated under reduced pressure. The residue was subjected to azeotropy with toluene and diethyl ether to remove excessive hydrobromic acid. The resulting white crystals were washed with diethyl ether to obtain 1.47 g of the title compound containing hydrogen bromide without purification.

Workup

  1. temperaturerefluxed
  2. customreturned to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customto remove excessive hydrobromic acid
  5. washThe resulting white crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-abe604bb0f394057b9f42fc8c9002ae5
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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