Sodium Hydroxide → 4-Bromoquinoline-6-carbonitrile

HRID 1437388Notes

Reaction equation

HRID 1437388 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][CH:4]=[CH:3]1.P(Br)(Br)[Br:15].[OH-].[Na+]>CN(C=O)C>[Br:15][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 116583514-Hydroxyquinoline-6-carbonitrile

Product 1

HCID 115214964-Bromoquinoline-6-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of quinolinone (b) (12.0 g, 70.5 mmol) in DMF (60 ml) was treated dropwise with phosphorus tribromide (8.0 ml, 84.6 mmol) over 10 minutes (exothermic). After allowing to stir and cool to room temperature, ice water (100 ml) was added and the mixture was stirred 30 minutes, then basified to pH8 by dropwise addition of 50% NaOH with cooling. The resultant solid was filterd off, washed with water and air dried to afford a tan solid (14.3 g, 87%).

Workup

  1. stirringthe mixture was stirred 30 minutes
  2. temperaturewith cooling
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-c390ae1c8dd440979a455252a9a7da2b
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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