Hydrochloric Acid → 2-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinic acid

HRID 1160829Notes

Reaction equation

HRID 1160829 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][N:23]=2)[C:17]([O:19]C)=[O:18])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)#[N:2].Cl>CO.C1COCC1.[OH-].[Na+]>[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][N:23]=2)[C:17]([OH:19])=[O:18])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)#[N:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66995160methyl 2-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinate

Product 1

HCID 669954272-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinic acidYield 99.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

100 mg of methyl 2-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinate was dissolved in a mixture of 2 ml of methanol and 3 ml of THF, and 66 μl of aqueous 1 M sodium hydroxide solution was added, followed by heating under reflux for 3 hours. The reaction mixture was cooled, then neutralized with 66 μl of 1 M hydrochloric acid, followed by extraction with a mixture of 2-propanol and chloroform (1:4). The organic layer was washed with brine. The solvent of the organic layer was evaporated under reduced pressure, and the resulting residue was recrystallized from a mixture of 2-propanol and chloroform (1:4) to obtain 95 mg of 2-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinic acid.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 3 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionfollowed by extraction with a mixture of 2-propanol and chloroform (1:4)
  6. washThe organic layer was washed with brine
  7. customThe solvent of the organic layer was evaporated under reduced pressure
  8. customthe resulting residue was recrystallized from a mixture of 2-propanol and chloroform (1:4)

Sources & evidence

ORD record
ord-dd4adeb9da824e7b9199e7b2f7a34814
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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