Potassium Hydroxide → 4-(4-Bromophenyl)quinolin-8-amine

HRID 432547Notes

Reaction equation

HRID 432547 reaction equation
O.O.[Sn](Cl)Cl.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:17](=[C:18]([N+:23]([O-])=O)[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[OH-].[K+]>C(O)C>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[N:16]=[CH:15][CH:14]=[C:13]2[C:10]1[CH:11]=[CH:12][C:7]([Br:6])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 187596114-(4-Bromophenyl)-8-nitroquinoline

Product 1

HCID 187596214-(4-Bromophenyl)quinolin-8-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tin (II) chloride dihydrate (9.50 g) and 4-(4-bromophenyl)-8-nitroquinoline (4.60 g) in 50 mL absolute ethanol was refluxed for 6 hours. The reaction mixture was cooled to room temperature and then made alkaline with 30% KOH solution. The precipitated solid was filtered off, and dissolved in chloroform. The filtrate was extracted with ether. The ether extract and chloroform solution were combined and dried over MgSO4. Evaporation gave a solid with 1H-NMR spectral signals consistent with 8-amino-4-(4-bromophenyl)quinoline.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. dissolutiondissolved in chloroform
  3. extractionThe filtrate was extracted with ether
  4. extractionThe ether extract
  5. dry with materialdried over MgSO4
  6. customEvaporation

Sources & evidence

ORD record
ord-b5f09c8ce54945038e4f919e1dc1730f
Source dataset
uspto-grants-2003_12
Patent number
US06664111B2

Reaction notes

Loading…