3-Chloroaniline → HCID 12588336, compound

HRID 242985Notes

Reaction equation

HRID 242985 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([NH:18][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 12588336HCID 12588336, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (317 mg, 2.0 mmol), 3-chlorophenylamine (0.212 mL, 2.0 mmol) and potassium carbonate (829 mg, 6.0 mmol) in DMF (3 mL) was heated at 140° C. for 30 min using microwave irradiation. After cooling to RT, the reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting brown oil (370 mg) was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane) to afford the title compound as a red solid (111 mg, 22%). LCMS (Method B): RT 3.95 min [M+H]+ 250.0.

Workup

  1. custommicrowave irradiation
  2. temperatureAfter cooling to RT
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc (×3)
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown oil (370 mg) was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane)

Sources & evidence

ORD record
ord-5ee833ae4df74ed38a2c01c08772423c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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