Hydrazine hydrate (1:1) → 3-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propylamine

HRID 1978006Notes

Reaction equation

HRID 1978006 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.O.NN>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[CH2:13][CH2:14][CH2:15][NH2:16])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219964552-[3-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propyl]isoindole-1,3-dione

Product 1

HCID 219964393-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propylamineYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[3-(7-methoxy-3,4-dihydronaphthalen-1-yl)propyl]isoindole-1,3-dione (11.8 g, 34.0 mmol) and hydrazine monohydrate (5.1 g, 0.1 mol) in ethanol (150 ml) was refluxed for 1 hour and then cooled in an ice bath. The resulting insoluble material was removed by filtration and the solvent was removed in vacuo to afford the titled compound (5.7 g, yield 77%, oil). This compound was provided for the next reaction without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting insoluble material was removed by filtration
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-af56849791bb4deca5d61a272d0fdf17
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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