Potassium Carbonate → HCID 86628212, compound

HRID 1821401Notes

Reaction equation

HRID 1821401 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].Br.[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26]Br)[CH3:23].C(OCC)(=O)C.[ClH:36]>CN(C=O)C.C(OCC)(=O)C>[ClH:36].[CH2:22]([N:24]([CH2:28][CH2:29][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14])[CH2:25][CH3:26])[CH3:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 706072-Bromoethyldiethylammonium bromideHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-HCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86628212HCID 86628212, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-hydroxy-3-methoxy-2-nitrobenzaldehyde (4.4 g, 22 mmol) in DMF (30 mL) was added with potassium carbonate (6.2 g, 24 mmol) and 2-(diethylamino)ethylbromide hydrobromide (6.2 g, 45 mmol), followed by stirring at 60° C. for 4 hours. Further, the reaction mixture was concentrated, added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to obtain crude product. The obtained product was dissolved in ethyl acetate and the solution was added with 4 mol/L hydrogen chloride-ethyl acetate solution. The obtained white crystal was collected by filtration and dried to obtain 4-(diethylamino) ethoxy-3-methoxy-2-nitrobenzaldehyde hydrochloride (2.2 g, 29%).

Workup

  1. concentrationFurther, the reaction mixture was concentrated
  2. additionadded with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto obtain crude product
  8. filtrationThe obtained white crystal was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-8a16f5c6f50547fc8bb56ab1a661e19f
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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