O-Toluidine → HCID 13143783, compound

HRID 242892Notes

Reaction equation

HRID 242892 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[NH2:18].CCN(CC)CC>CN(C=O)C>[N+:8]([C:7]1[C:2]([NH:18][C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:11])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7242O-Toluidine2×HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 13143783HCID 13143783, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (4.13 g, 26.1 mmol), o-tolylamine (3.4 mL, 31.3 mmol) and Et3N (4.4 mL, 31.3 mmol) in DMF (10 mL) was stirred at 90° C. for 1 h under a nitrogen atmosphere. Additional o-tolylamine (2 mL, 18.2 mmol) was added and stirring continued for 16 h. The mixture was partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 20-100% DCM in cyclohexane) to afford the title compound as an orange solid (3.96 g, 66%). LCMS (Method C): RT 3.60 min [M+H]+ 230.3

Workup

  1. stirringstirring
  2. waitcontinued for 16 h
  3. customThe mixture was partitioned between DCM and water
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. washthe combined organic fractions washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 20-100% DCM in cyclohexane)

Sources & evidence

ORD record
ord-9ed781bbd0ae4861a3c1ebba982c4d9d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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