Isopropanol → 2-Amino-3-bromo-4-(4-amino-3-chlorophenoxy)pyridine

HRID 1433475Notes

Reaction equation

HRID 1433475 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.[Br:17]N1C(=O)CCC1=O.C(O)(C)C>O>[NH2:1][C:2]1[C:7]([Br:17])=[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

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 67184N-bromobutanimideHCID 229367984-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine

Product 1

HCID 229362552-Amino-3-bromo-4-(4-amino-3-chlorophenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-(4-amino-3-chlorophenoxy)pyridine (1.0 g), N-bromosuccinimide (0.78 g) and isopropanol (10 ml) were stirred for 15 minutes under reflux. 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 (hexane:ethyl acetate=2:1, followed by 1:1, ethyl acetate) to obtain 400 mg of the target substance as a brown oil.

Workup

  1. temperatureunder reflux
  2. customwas returned to room temperature
  3. extractionextraction
  4. additionSilica gel was added to the extract solution
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionThe silica gel was charged into a dry column
  7. custompacked with silica gel, and purification
  8. customto obtain 400 mg of the target substance as a brown oil

Sources & evidence

ORD record
ord-d34ebccc56ee459ea3e9e0fdf4f96c13
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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