Hydrazine hydrate (1:1) → 6-(Quinolin-3-yl)hexan-1-amine

HRID 1583436Notes

Reaction equation

HRID 1583436 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH:2]=1.O.NN>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135575552-[6-(Quinolin-3-yl)hexyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 135575486-(Quinolin-3-yl)hexan-1-amineYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Quinolinehexanamine was prepared in the same manner as described in Example 110, starting from 4.4 g of 2-[6-(3-quinolinyl)hexyl]-1H-isoindole-1,3(2H)-dione and 2.5 g of hydrazine hydrate in 60 ml of ethanol. The crude product was evaporatively distilled to give 2.5 g (89%) of 3-quinolinehexanamine, bp 144°-155° C./0.1 mm. Bis picrate mp 225°-226° C.

Workup

  1. custom3-Quinolinehexanamine was prepared in the same manner
  2. distillationThe crude product was evaporatively distilled

Sources & evidence

ORD record
ord-21745a1fab1441a99373208ceaf63d74
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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