4-Nitrophenol → 3-Iodo-4-(4-nitrophenoxy)-2-pyridinamine

HRID 1010179Notes

Reaction equation

HRID 1010179 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:9].[CH:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[I:9][C:3]1[C:4]([NH2:8])=[N:5][CH:6]=[CH:7][C:2]=1[O:19][C:12]1[CH:11]=[CH:10][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 229365964-Chloro-3-iodopyridin-2-amine

Product 1

HCID 229363343-Iodo-4-(4-nitrophenoxy)-2-pyridinamineYield 38.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-3-iodo-2-pyridinamine (1.0 g), p-nitrophenol (1.1 g), diisopropylethylamine (1.0 ml) and N-methyl-2-pyrrolidone (2 ml) were stirred at 170° C. for 17 hours. After returning the reaction solution to room temperature, water was added and extraction was performed with ethyl acetate. NH type silica gel was added to the extract, the solvent was distilled off under reduced pressure, and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (hexane:ethyl acetate=3:1). The solvent was distilled off under reduced pressure, and then ethyl acetate and hexane were added to the residue for solidification to obtain 540 mg of light yellow crystals.

Workup

  1. customto room temperature
  2. extractionextraction
  3. additionNH type silica gel was added to the extract
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with NH type silica gel, and column purification
  7. distillationThe solvent was distilled off under reduced pressure
  8. additionethyl acetate and hexane were added to the residue for solidification

Sources & evidence

ORD record
ord-c0733bd12a934304b5abbc6a57e174cb
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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