Isopropanol → 2-Amino-4-(4-amino-3,5-dichlorophenoxy)pyridine

HRID 387824Notes

Reaction equation

HRID 387824 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:17]N1C(=O)CCC1=O.C(O)(C)C>O>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[C:13]([Cl:17])[C:12]([NH2:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 31398ChlorosuccinimideHCID 229367984-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine

Product 1

HCID 229363272-Amino-4-(4-amino-3,5-dichlorophenoxy)pyridineYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-(4-amino-3-chlorophenoxy)pyridine (700 mg), N-chlorosuccinimide (0.44 g) and isopropanol (10 ml) were stirred at 80° C. for 1 hour. The mixture was returned to room temperature, water was added, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (ethyl acetate), to obtain 120 mg of a brown oil.

Workup

  1. customwas returned to room temperature
  2. extractionextraction
  3. additionSilica gel was added to the extract solution
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with silica gel, and purification

Sources & evidence

ORD record
ord-fec1ac269d7447ce81dd340ad3d95fbe
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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