8-Bromo-5-nitroquinoline → 8-Bromoquinolin-5-amine

HRID 1017126Notes

Reaction equation

HRID 1017126 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2>C(O)(=O)C.C(O)C.[Fe]>[NH2:12][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

5

Reactant 1

HCID 157091828-Bromo-5-nitroquinoline

Product 1

HCID 129500548-Bromoquinolin-5-amine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

At reflux, 10.0 g of 8-bromo-5-nitroquinoline in 68 ml of glacial acetic acid and 34 ml of ethanol were added dropwise to a mixture of 7.75 g of iron powder, 18 ml of glacial acetic acid and 9 ml of ethanol. After stirring for 45 minutes at reflux, the mixture was cooled and filtered through diatomaceous earth. The filtrate was concentrated, taken up in methylene chloride, washed with sodium carbonate solution, dried and concentrated.

Workup

  1. temperatureAt reflux
  2. temperatureat reflux
  3. temperaturethe mixture was cooled
  4. filtrationfiltered through diatomaceous earth
  5. concentrationThe filtrate was concentrated
  6. washwashed with sodium carbonate solution
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c72f3adff2f42ddbd206d852b117612
Source dataset
uspto-grants-2002_11
Patent number
US06479436B1

Reaction notes

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