Hydrochloric Acid → 5-Bromo-6-cyanopyridine-2-carboxylic acid

HRID 474198Notes

Reaction equation

HRID 474198 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([C:12]#[N:13])[N:6]=1)=[O:4].Cl>C1COCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57356968Methyl 5-bromo-6-cyanopyridine-2-carboxylate

Product 1

HCID 574252995-Bromo-6-cyanopyridine-2-carboxylic acidYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of potassium trimethylsilanoate (0.80 g, 6.22 mmol) in THF (26 mL) was added 5-bromo-6-cyano-pyridine-2-carboxylic acid methyl ester (998 mg, 4.15 mmol). The mixture was heated at 50° C. for 3 h, then was cooled to rt and treated with HCl (4 N in dioxane; 1.60 mL). After 30 min, the mixture was concentrated. The residue was dissolved in hot EtOAc and filtered. The filtrate was concentrated to give the title compound (993 mg, >100%), which was used in the next step without further purification.

Workup

  1. temperaturewas cooled to rt
  2. concentrationthe mixture was concentrated
  3. dissolutionThe residue was dissolved in hot EtOAc
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-91c71256c99440658fb70c75f9f02a8f
Source dataset
uspto-grants-2014_01
Patent number
US08637520B2

Reaction notes

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