4-Chloro-6,7-dimethoxy-3-nitroquinoline → HCID 22646632, compound

HRID 393623Notes

Reaction equation

HRID 393623 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:16]([O-])=O>C(O)C.[Ni]>[NH2:16][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Cl:1])=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2

Participants

4

Reactant 1

HCID 226465674-Chloro-6,7-dimethoxy-3-nitroquinoline

Product 1

HCID 22646632HCID 22646632, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-chloro-6,7-dimethoxy-3-nitroquinoline (1.07 g, 4 mmol) in ethanol (40 ml) containing Raney Nickel (1 g) was stirred under hydrogen at atmospheric pressure for 3 hours. The volatiles were removed by evaporation. The residue was triturated with petroleum ether, collected by filtration and dried under vacuum to give 3-amino-4-chloro-6,7-dimethoxyquinoline (925 mg, 97%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customThe residue was triturated with petroleum ether
  3. filtrationcollected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-110887393d7547dca4f2b0f51996549d
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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