Acetic Acid → 2-[[4-(Methylthio)phenyl]amino]isonicotinic acid

HRID 452631

Reaction equation

HRID 452631 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH3:11][S:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH3:11][S:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 660384-(Methylthio)anilineHCID 3453602-Fluoroisonicotinic acid

Product 1

HCID 284003552-[[4-(Methylthio)phenyl]amino]isonicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-fluoroisonicotinic acid (620 mg, 4.95 mmol) and 4-(methylthio)aniline (0.984 mL, 8.42 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (792 mg, 19.8 mmol), and the resulting mixture was stirred under an argon atmosphere at 85° C. for 5 hr. After cooling, acetic acid (1.2 mL) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Ethyl acetate and water were added to the residue, the mixture was stirred for 20 min, and the precipitate was collected by filtration to give crude 2-[[4-(methylthio)phenyl]amino]isonicotinic acid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. stirringthe mixture was stirred for 20 min
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-421b9b0c69434c2cabddaf72f72d3971
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Linked notes

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