Water → 4-(4-Aminophenoxy)-2-butylaminopyridine

HRID 387791Notes

Reaction equation

HRID 387791 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=O)[CH2:15][CH2:16][CH3:17])[CH:8]=2)=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O>O1CCCC1>[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 229364634-(4-Aminophenoxy)-2-butyrylaminopyridine

Product 1

HCID 229369234-(4-Aminophenoxy)-2-butylaminopyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 80 mg of 4-(4-aminophenoxy)-2-butyrylaminopyridine in 8 ml of tetrahydrofuran, 67 mg of aluminum lithium hydride was added while stirring at room temperature, and the mixture was stirred at 70° C. for 10 minutes. Water was added, extraction was performed with ethyl acetate, and then silica gel was added to the extract and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purified by column chromatography (ethyl acetate) to obtain 54 mg of the target substance as a brown oil.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 70° C. for 10 minutes
  3. extractionextraction
  4. additionsilica gel was added to the
  5. extractionextract
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionThe silica gel was charged into a dry column
  8. custompurified by column chromatography (ethyl acetate)
  9. customto obtain 54 mg of the target substance as a brown oil

Sources & evidence

ORD record
ord-f220f6643bf34d84be796c82d8132202
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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