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

HRID 1010211Notes

Reaction equation

HRID 1010211 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-2e152a47522b49a89defefc59a41dfc5
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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