Aniline → HCID 3785006, compound

HRID 598737Notes

Reaction equation

HRID 598737 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:11][C:4]1[N:3]=[C:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 3785006HCID 3785006, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (772 mg, 4 mmol), aniline (364 μL, 4 mmol) and DIEA (838 μL, 24.8 mmol) in 10 mL THF was stirred at r.t. for 70 h. After removal of the solvent, the residue was dissolved in DCM, and subjected to silica gel column purification to give 735 mg (yield 74%) of the title compound. LC-MS: Calculated mass=249. Observed mass=250.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. customsubjected to silica gel column purification

Sources & evidence

ORD record
ord-b20a4881cc4c42459fb1e6f1c45225d3
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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