2-Hydroxyquinoline → HCID 21873633, compound

HRID 1782016Notes

Reaction equation

HRID 1782016 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=O.P(Br)(Br)[Br:13].[C:16](=[O:19])([O-])[O-].[Na+].[Na+].CN([CH:25]=[O:26])C>>[Br:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]3[O:19][CH2:16][CH2:25][O:26][C:6]3=2)[N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 4

HCID 60382-HydroxyquinolineHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24614Phosphorus tribromide

Product 1

HCID 21873633HCID 21873633, compound

Procedure

The quinolinone (4d) in dry DMF (8 mL) was cooled in ice and phosphorus tribromide (0.7 mL) added drop-wise, and the mixture was stirred, with ice-cooling for 30 minutes then allowed to warm to room temperature and stirred for a further 2 hours. It was cooled in ice and sodium carbonate solution was added and the solid was collected, washed well with water, and dried in vacuo, to afford a pale yellow solid (1.65 g).

Workup

  1. temperaturecooling for 30 minutes
  2. stirringstirred for a further 2 hours
  3. temperatureIt was cooled in ice
  4. customthe solid was collected
  5. washwashed well with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-921de28713984b36864e4ef621b2a860
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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