Toluene → 3-Nitro-6-phenylpyridin-2-amine

HRID 1437463Notes

Reaction equation

HRID 1437463 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C.O1CCCC1.O1CCCC1>[N+:9]([C:5]1[C:6]([NH2:8])=[N:7][C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1)([O-:11])=[O:10]

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 105606193-Nitro-6-phenylpyridin-2-amineYield 53%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon stream, a mixture of 6-chloro-3-nitro-2-pyridine amine (2.0 g), phenylboric acid (2.1 g), tetrakis(triphenylphosphine)palladium(0) (1.3 g), 2 M sodium carbonate (35 ml), toluene (40 ml) and tetrahydrofuran (20 ml) was stirred at 90° C. for 12 hours. The mixture was distributed into ethyl acetate-tetrahydrofuran (3:1, v/v) and water. The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure and the resulting crystals were collected by filtration to obtain 3-nitro-6-phenyl-2-pyridine amine (1.3 g, 53%).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. distillationThe solvent was distilled off under reduced pressure
  4. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-6fa2f26bc55a48d4927428721dc2d765
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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