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

HRID 2220015Notes

Reaction equation

HRID 2220015 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([N+:18]([O-])=O)[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[C:13]([NH2:18])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 187596114-(4-Bromophenyl)-8-nitroquinoline

Product 1

HCID 187596214-(4-Bromophenyl)quinolin-8-amineYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4-Bromophenyl)-8-nitroquinoline (30 g, 91.1 mmol) was added to absolute ethanol (120 mL) and purged with nitrogen. To this was added tin (II) chloride (190 mmol) and the reaction mixture refluxed for 4 hours. The pH was adjusted to 12 with aqueous NaOH and the organics were extracted using methylene chloride. The organics were then purified on basic alumina (methylene chloride/methanol 99:1) to yield 21.2 g of 4-(4-bromophenyl)quinolin-8-yl amine.

Workup

  1. custompurged with nitrogen
  2. temperaturethe reaction mixture refluxed for 4 hours
  3. extractionthe organics were extracted
  4. customThe organics were then purified on basic alumina (methylene chloride/methanol 99:1)

Sources & evidence

ORD record
ord-9332cfe952244ef4b9a8c8596ec4a924
Source dataset
uspto-grants-2008_08
Patent number
US07416791B1

Reaction notes

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