Hydrogen Bromide → HCID 178510513, compound

HRID 750746Notes

Reaction equation

HRID 750746 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([O:10]C)[C:3]=1[C:4]#[N:5].[BrH:12]>C(O)(=O)C>[Br:12][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14709302-Chloro-4-methoxynicotinonitrile

Product 1

HCID 178510513HCID 178510513, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-4-methoxy-nicotinonitrile (M. Mittelbach et al., Arch. Pharm. (Weinheim Ger.); 1985, GE, 318, 6, 481-486) (6.92 g) was suspended in 70 mL of 30% HBr in acetic acid in a pressure vessel and heated with stirring at 100° C. for 2 h. The reaction was cooled to room temperature and filtered, washing well with H2O, and dried in vacuo overnight at 50° C. providing 4.85 g 2-bromo-4-hydroxy-nicotinonitrile as a white solid. Proton NMR(DMSO) indicated the product was a mixture of 69% bromo compound with 31% starting chloro analog.

Workup

  1. temperatureheated
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washwashing well with H2O
  5. customdried in vacuo overnight at 50° C.

Sources & evidence

ORD record
ord-1232be2f043b4386b1313ee99d86a362
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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