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

HRID 582198Notes

Reaction equation

HRID 582198 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 mixture 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.) was heated in ethanol (150 ml) for one hour under reflux. The reaction mixture was ice-cooled, then resulting insolubles were filtered off. The filtrate was concentrated under reduced pressure to afford the titled compound (5.7 g, yield 77%, oily). This compound was used for the subsequent reaction without further purification.

Workup

  1. temperatureunder reflux
  2. temperaturecooled
  3. filtrationresulting insolubles were filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f793a16570f49409b5254c490d9fa43
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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