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

HRID 1160831Notes

Reaction equation

HRID 1160831 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][N:29]=2)[C:23]([O:25]C)=[O:24])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[N:10]1)#[N:2].[OH-].[Na+].Cl>CO.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][N:29]=2)[C:23]([OH:25])=[O:24])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:11]=[N:10]1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68622689methyl 2-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinate

Product 1

HCID 686215802-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinic acidYield 34.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

12 mg of methyl 2-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinate was dissolved in a mixture of 234 μl of methanol and 351 μl of THF, then 61 μl of aqueous 1 M sodium hydroxide solution was added, followed by heating under reflux for 3 hours. The reaction mixture was cooled, and neutralized with 61 μl of 1 M hydrochloric acid, then extracted with a mixture of 2-propanol and chloroform (1:4). The organic layer was washed with brine. The solvent of the organic layer was removed under reduced pressure, and the resulting residue was recrystallized from a mixture of 2-propanol and chloroform (1:4) to obtain 4 mg of 2-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinic acid.

Workup

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

Sources & evidence

ORD record
ord-fdc17089b8434eb19a521fd4204c00f3
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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