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

HRID 1433441Notes

Reaction equation

HRID 1433441 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-].[Al+3].[Li+].[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 lithium aluminum 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-9f19a268e35b4522aeedd286c09acfe9
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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