m-Toluidine → HCID 22724072, compound

HRID 242934Notes

Reaction equation

HRID 242934 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1([CH3:18])[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1.CCN(CC)CC>CN(C=O)C>[N+:8]([C:7]1[C:2]([NH:17][C:13]2[CH:12]=[C:11]([CH3:18])[CH:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 22724072HCID 22724072, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (2.28 g, 14.4 mmol), m-tolylamine (2.78 g, 25.9 mmol) and Et3N (3.6 mL, 25.9 mmol) in DMF (10 mL) was stirred at 90° C. for 16 h under a nitrogen atmosphere. The reaction mixture was partitioned between DCM and water. The aqueous phase was extracted with DCM (×3) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in cyclohexane) to afford the title compound as an orange solid (2.31 g, 70%). LCMS (Method C): RT 3.81 min [M+H]+ 230.1.

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. extractionThe aqueous phase was extracted with DCM (×3)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in cyclohexane)

Sources & evidence

ORD record
ord-4714cda42ec9457984f52d1b0ae15f7c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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