Hydrochloric Acid → 5-Cyanopyridine-2-carboxylic acid

HRID 2281838Notes

Reaction equation

HRID 2281838 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][N:6]=1)=[O:4].[OH-].[Na+].Cl>C(O)C>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1)#[N:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 45082467Methyl 5-cyanopyridine-2-carboxylate

Product 1

HCID 124007345-Cyanopyridine-2-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl-5-cyanopyridine-2-carboxylate (920 mg) and a 5 N NaOH solution (2.26 mL) in ethanol (30 mL) was stirred at RT for 10 min. 5 N hydrochloric acid (5.2 mL) was added to the reaction solution at RT, followed by extraction with EtOAc. The extract was dried over anhydrous MgSO4. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (800 mg). 1H-NMR (400 MHz, DMSOd6) δ (ppm): 8.18 (d, J=8.0 Hz, 1H), 8.51 (dd, J=2.0, 8.0 Hz, 1H), 9.12-9.18 (m, 1H).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe extract was dried over anhydrous MgSO4
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f59fc3df619649d8820b998a681036af
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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