Ethyl Acetate → 4-[(Pyridin-4-yl)sulfanyl]butan-1-amine

HRID 864003Notes

Reaction equation

HRID 864003 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)C(=O)C2=CC=CC=C12.O.NN.C(OCC)(=O)C>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 14538888HCID 14538888, compound

Product 1

HCID 135575374-[(Pyridin-4-yl)sulfanyl]butan-1-amineYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 12.50 g (40 mmol) of 4-(4-phthalimidobutylthio)pyridine in 200 ml of ethanol, 5.82 ml (120 mmol) of hydrazine monohydrate was added, and the mixture was stirred at room temperature for 4 hours. Then, ml of ethyl acetate was-added, and the insoluble material was filtered off. The volatile components were distilled off and chloroform was added to the residue. The mixture was washed with saturated saline and dried over potassium carbonate. The solvent was distilled off and 7.30 g of the desired compound were obtained (quantitative yield, yellow oil).

Workup

  1. additionwas added
  2. filtrationthe insoluble material was filtered off
  3. distillationThe volatile components were distilled off
  4. additionchloroform was added to the residue
  5. washThe mixture was washed with saturated saline
  6. dry with materialdried over potassium carbonate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9c85ea88184648d589d8e25d62818aa0
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Reaction notes

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