Ethanol → 6,7-Dimethoxy-4-(3-aminopropoxy)quinoline

HRID 387741Notes

Reaction equation

HRID 387741 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][CH2:16][CH2:17][CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O.O.NN.C(O)C.CO>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][CH2:16][CH2:17][CH2:18][NH2:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 22936492N-(3-(6,7-dimethoxyquinolin-4-yloxy)propyl)phthalimide

Product 1

HCID 229362886,7-Dimethoxy-4-(3-aminopropoxy)quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3-(6,7-Dimethoxyquinolin-4-yloxy)propyl)phthalimide (600 mg, 1.53 mM), hydrazine monohydrate (300 mg, 6.12 mM), ethanol (5 ml), methanol (5 ml) and tetrahydrofuran (5 ml) were stirred for 2 hours under reflux. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (Fuji Silicia NH Type Silica Gel, chloroform:methanol=20:1) to obtain the target substance (150 mg) as a brown oil.

Workup

  1. temperatureunder reflux
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel chromatography (Fuji Silicia NH Type Silica Gel, chloroform:methanol=20:1)
  4. customto obtain the target substance (150 mg) as a brown oil

Sources & evidence

ORD record
ord-dfeaa0df382d454a858f69a7c6d066f9
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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