Potassium Carbonate → HCID 22144870, compound

HRID 1824922Notes

Reaction equation

HRID 1824922 reaction equation
[OH:1][C:2]1[C:9]([Br:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+:18].[K+].Br[CH:21](C(OCC)=O)[C:22]([O:24]CC)=[O:23]>CC(=O)CC>[N+:11]([C:7]1[CH:8]=[C:9]([Br:10])[C:2]2[O:1][C:21]([C:22]([O-:24])=[O:23])=[CH:4][C:3]=2[CH:6]=1)([O-:13])=[O:12].[K+:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 5193073-Bromo-2-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 22144870HCID 22144870, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 11.0 gm (44.7 mMol) 2-hydroxy-3-bromo-5-nitrobenzaldehyde, 5.56 gm (40.24 mMol) potassium carbonate, and 8.0 mL (46.95 mMol) diethyl bromomalonate in 55 mL 2-butanone was heated at reflux for 5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between 450 mL diethyl ether and 250 mL water and the aqueous phase was adjusted to pH of about 1 by the addition of dilute sulfuric acid. The phases were separated and the aqueous phase was extracted with two 150 mL portions of diethyl ether. The organic phases were combined, washed with 50 mL saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residual solid was dissolved in 200 mL ethanol to which were added 4.8 gm (85.5 mMoL) potassium hydroxide. The resulting suspension was warmed on a steam bath for 1 hour. The suspension was then cooled to room temperature. After about 18 hours the mixture was filtered and dried under reduced pressure to provide 14.1 gm (98%) of the desired compound as an orange solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 450 mL diethyl ether and 250 mL water
  5. additionthe aqueous phase was adjusted to pH of about 1 by the addition of dilute sulfuric acid
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted with two 150 mL portions of diethyl ether
  8. washwashed with 50 mL saturated aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe residual solid was dissolved in 200 mL ethanol to which
  12. additionwere added 4.8 gm (85.5 mMoL) potassium hydroxide
  13. temperatureThe resulting suspension was warmed on a steam bath for 1 hour
  14. temperatureThe suspension was then cooled to room temperature
  15. filtrationAfter about 18 hours the mixture was filtered
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-f0d42ad8ab324eaaad2d53c5de86ea44
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

Loading…