Potassium Carbonate → HCID 11708505, compound

HRID 1168838Notes

Reaction equation

HRID 1168838 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]([CH3:25])[CH3:24]>CN(C)C=O.C(OC(C)C)(C)C>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 11708505HCID 11708505, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 7914Diisopropyl EtherSolvent

Procedure

10 mmol of 5-hydroxy-2-nitrobenzaldehyde dissolved in dimethylformamide are added dropwise to 20 mmol of potassium carbonate suspended in a mixture of dimethyl-formamide and isopropyl ether, and then the reaction mixture is heated at reflux for 2 hours. After the mixture has returned to ambient temperature, 10 mmol of 2-chloro-N,N-dimethylethanamine hydrochloride are added dropwise, and then the reaction mixture is heated at reflux again for one night. After returning to ambient temperature, the mixture is filtered and the solvents of the filtrate are evaporated off to yield the expected product in the form of an oil.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. customhas returned to ambient temperature
  4. temperaturethe reaction mixture is heated
  5. temperatureat reflux again for one night
  6. customAfter returning to ambient temperature
  7. filtrationthe mixture is filtered
  8. customthe solvents of the filtrate are evaporated off

Sources & evidence

ORD record
ord-88095e7f64f34fe7a4e6d8000297919d
Source dataset
uspto-grants-2003_09
Patent number
US06627650B2

Reaction notes

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