Phosphorus trichloride → N-(4-Methoxybenzyl)-4-nitropyridin-2-amine

HRID 1640105Notes

Reaction equation

HRID 1640105 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9]2[N+:10]([O-])=[CH:11][CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][N:10]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 178490962HCID 178490962, compound

Product 1

HCID 58902405N-(4-Methoxybenzyl)-4-nitropyridin-2-amineYield 108.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a 2 L 3 neck round bottom flask fitted with a mechanical stirrer, was added N-(4-methoxybenzyl)-4-nitropyridin-2-amine 1-oxide (38.72 g, 0.14 mol) and chloroform (580 mL). The reaction mixture was cooled to 0° C. and phosphorus trichloride (36.8 mL, 0.42 mol) was added dropwise. The reaction mixture was allowed to warm to rt and stir overnight. The reaction mixture was filtered and the resulting solid was slurried with hexanes and filtered (repeated several times) to afford N-(4-methoxybenzyl)-4-nitropyridin-2-amine (39.34 g, 102%) as a yellow solid. LCMS: (FA) ES+ 260.3.

Workup

  1. temperatureto warm to rt
  2. filtrationThe reaction mixture was filtered
  3. filtrationfiltered (repeated several times)

Sources & evidence

ORD record
ord-29622bb1ff824b41bc0c3e1ef1326ac7
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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