Potassium Carbonate → Methyl 4-amino-3-(propylamino)benzoate

HRID 1174008Notes

Reaction equation

HRID 1174008 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([NH2:12])=[C:2]([NH:1][CH2:20][CH2:21][CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 23155569Methyl 4-amino-3-(propylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (40 ml), methyl 3,4-diaminobenzoate (2.01 g) was dissolved and then the solution was added with potassium carbonate (2.00 g) and 1-iodopropane (1.4 ml), followed by stirring at room temperature for 22 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate and washed with water, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.06 g).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-684b7b64173e4eca848146bb5364518a
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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