4-Nitrophenol → 4-(4-Nitrophenoxy)pyridin-2-amine

HRID 387921Notes

Reaction equation

HRID 387921 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([OH:18])[CH:10]=1.CCN(C(C)C)C(C)C.CN1CCCC1=O>O>[NH2:1][C:2]1[CH:7]=[C:6]([O:18][C:11]2[CH:10]=[CH:9][C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 15.88 g of 2-amino-4-chloropyridine 34.5 g of p-nitrophenol, 52 ml of Hunig's base and 100 ml of 1-methyl-2-pyrrolidinone was stirred at 160° C. for 15 hours. Water was added, extraction was performed with ethyl acetate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=1:1) using NH type silica gel to obtain 3.24 g of the target substance as a light yellow solid.

Workup

  1. extractionextraction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by column chromatography (hexane:ethyl acetate=1:1)
  4. customto obtain 3.24 g of the target substance as a light yellow solid

Sources & evidence

ORD record
ord-75b8456bb4384727b67e39bdef97c897
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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