Hydrazine hydrate (1:1) → 3-(Pyridin-3-yl)propan-1-amine

HRID 1583397Notes

Reaction equation

HRID 1583397 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH:2]=1.O.NN>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][NH2:10])[CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135575522-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 135575233-(Pyridin-3-yl)propan-1-amineYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11.3 g of 2-[3-(3-pyridyl)propyl]-1H-isoindole-1,3(2H)-dione and 10.1 g of hydrazine hydrate was refluxed in 200 ml of ethanol for 6 hours, allowed to cool, and was filtered. The filtrate was concentrated and the residue distilled to give 4.77 g (70%) of 3-pyridinepropanamine, bp 84°-86° C./0.35 mm.

Workup

  1. temperatureto cool
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-fcbc6f61b72c42cc80c77c5ac8c63246
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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