Ethyl Acetate → 4-(3-Aminopropoxy)pyridine

HRID 274683Notes

Reaction equation

HRID 274683 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)C(=O)C2=CC=CC=C12.C(OCC)(=O)C>C(O)C>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 190790904-(3-Phthalimidopropyloxy)pyridine

Product 1

HCID 149941254-(3-Aminopropoxy)pyridineYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate [2.99 ml (61.6 mmol)] was added to a suspension of 5.80 g (20.5 mol) of 4-(3-phthalimidopropyloxy)pyridine in 50 ml of ethanol, and the mixture was stirred at room temperature for 3 hours. 100 ml of ethyl acetate was added and insoluble materials were filtered off. The volatile component in the filtrate was distilled off and then chloroform was added to the residue. The mixture was washed with brine and dried over potassium carbonate. The solvent was distilled off to obtain 2.99 g of the desired compound (yield: 99.5%, pale yellow oil).

Workup

  1. filtrationinsoluble materials were filtered off
  2. distillationThe volatile component in the filtrate was distilled off
  3. additionchloroform was added to the residue
  4. washThe mixture was washed with brine
  5. dry with materialdried over potassium carbonate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-4d837498b23c45b7ab0a2adebf773c7f
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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