Sodium Bicarbonate → 6-Bromocinnoline

HRID 2307780Notes

Reaction equation

HRID 2307780 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[C:5]2NN.C([O-])(O)=O.[Na+]>O.[O-]S([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 226071766-Bromo-4-hydrazinylcinnoline

Product 1

HCID 112295606-BromocinnolineYield 24%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

A solution of Example 34E (3.5 g, 14 mmol) in water (50 mL) was heated to reflux, treated dropwise with a solution of CuSO4 (2.8 g, 17.5 mmol) in water (20 mL), refluxed for 2 hours, cooled to room temperature, adjusted to pH 7 with saturated NaHCO3 (aq), and extracted with ethyl acetate (2×25 mL). The combined extracts were concentrated and the residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide the desired product (0.7 g, 24%).

Workup

  1. temperatureto reflux
  2. temperaturerefluxed for 2 hours
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. concentrationThe combined extracts were concentrated
  5. customthe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-51812ec4500a47b59a9bb389d4fa3f56
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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