Potassium Carbonate → 4-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

HRID 571102Notes

Reaction equation

HRID 571102 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([CH3:19])[C:11]=1[CH3:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:20][C:11]1[C:12]([CH3:19])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 247212012,3-Dimethyl-4-fluoronitrobenzeneHCID 178507942HCID 178507942, compound

Product 1

HCID 585648204-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 2-aminopyridin-4-ol (600 mg, 5.5 mmol) and 1-fluoro-2,3-dimethyl-4-nitrobenzene (570 mg, 3.37 mmol) in DMSO (4.0 mL) was added K2CO3 (1.00 g, 7.20 mmol) and the reaction mixture heated to 75° C. for 3 days. The resulting mixture was cooled to RT and was partitioned between water (50 mL) and EtOAc (75 mL). The aq layer was separated and extracted with EtOAc (75 mL) and the combined organic extracts were washed with water (3×50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was recrystallized from DCM to afford the title compound, Intermediate C2, as a tan solid (25 mg, 28%): Rt 1.40 min (Method 2); m/z 260 (M+H)+ (ES+).

Workup

  1. temperatureThe resulting mixture was cooled to RT
  2. customwas partitioned between water (50 mL) and EtOAc (75 mL)
  3. customThe aq layer was separated
  4. extractionextracted with EtOAc (75 mL)
  5. washthe combined organic extracts were washed with water (3×50 mL) and brine (50 mL)
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from DCM

Sources & evidence

ORD record
ord-7b22dc1deb2b434bab6d460d4a591949
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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