Hydrazine hydrate (1:1) → (E)-4-(4-isoquinolinyl)-3-buten-1-amine

HRID 2073320Notes

Reaction equation

HRID 2073320 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:12]/[CH2:13][CH2:14]C2C3C(=CC=CC=3)C=N2)=[CH:3][N:2]=1.O.[NH2:25]N>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:12]/[CH2:13][CH2:14][NH2:25])=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86743857(E)-1-[4-(4-isoquinolinyl)-3-butenyl]-1H-isoindole

Product 1

HCID 14750834(E)-4-(4-isoquinolinyl)-3-buten-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a refluxing solution of 1.75 g of (E)-1-[4-(4-isoquinolinyl)-3-butenyl]-1H-isoindole-1,3-(2H-dione in 80 mL of ethanol was added 1.1 mL of hydrazine hydrate and the reaction was stirred at reflux for 17 hours. The solvent was removed in vacuo and the residue was triturated with chloroform. The extract was concentrated to yield 1 g of (E)-4-(4-isoquinolinyl)-3-buten-1-amine as an oil.

Workup

  1. temperatureat reflux for 17 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was triturated with chloroform
  4. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-4c23bb3e0cd44128bb129edd420eb3ae
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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