Hydrazine hydrate (1:1) → 8-Isoquinolinepropanamine

HRID 1110481Notes

Reaction equation

HRID 1110481 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:4]=[CH:3][N:2]=1.O.NN>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][CH2:13][NH2:14])[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14347502[3-(8-isoquinolinyl)propyl]-1H-isoindole-1,3-(2H)-dione

Product 1

HCID 149941278-IsoquinolinepropanamineYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a refluxing solution of 0.174 g of [3-(8-isoquinolinyl) propyl]-1H-isoindole-1,3-(2H)-dione in 8 mL of ethanol was added 0.12 mL of hydrazine hydrate and the reaction was stirred at reflux for 5.5 hours. The solvent was removed under reduced pressure and the residue was triturated with chloroform. The chloroform extract was concentrated to an oil which was passed through a short column of silica gel (chloroform-methanoltriethylamine; 1:4:15) to yield 0.103 g of 8-isoquinolinepropanamine as an oil.

Workup

  1. temperatureat reflux for 5.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was triturated with chloroform
  4. extractionThe chloroform extract
  5. concentrationwas concentrated to an oil which

Sources & evidence

ORD record
ord-8281f068dce448e186a8a32fb796b81f
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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