Phosphorus oxychloride → Benzyl-(2-chloro-3-nitro-pyridin-4-yl)-amine

HRID 639686Notes

Reaction equation

HRID 639686 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](O)[C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([Cl:21])[C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526800HCID 178526800, compound

Product 1

HCID 72697848Benzyl-(2-chloro-3-nitro-pyridin-4-yl)-amineYield 89.3%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

4-benzylamino-3-nitro-pyridin-2-ol (6.15 g, 25.07 mmol) was suspended in 100 mL of acetonitrile then phosphorus oxychloride (12 mL, 125.40 mmol) was added followed by tetraethyl ammonium chloride (4.15 g, 25.07 mmol) and the mixture was stirred at 85° C. overnight. The solvent was removed in vacuo and the residue was suspended in water (300 mL) and extracted with dichloromethane (2×200 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give 5.9 g of the title compound as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with dichloromethane (2×200 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7a553537354c49c4bd15ef6212e3b2da
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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