Sulfuric Acid → Benzoic acid, 4-[3-(4-aminophenyl)propyl]-, methyl ester

HRID 2176005Notes

Reaction equation

HRID 2176005 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH:11]=[CH:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.S(=O)(=O)(O)O>[C].[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 3918365HCID 3918365, compound

Product 1

HCID 68207867Benzoic acid, 4-[3-(4-aminophenyl)propyl]-, methyl esterYield 67%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 5.0 g of methyl 4-[3-(4-nitrophenyl)-3-oxoprop-1-en-1-yl]benzoate and 150 mL of methanol was added dropwise 5.0 mL of concentrated sulfuric acid under ice cooling. In an argon atmosphere, 500 mg of 10% palladium carbon was added to the reaction mixture. After hydrogen (3 atm) purging was performed at room temperature, the mixture was stirred for 24 hours. The insoluble material was removed by filtration by using celite, and then the filtrate was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue under ice cooling to neutralize the residue, and then extraction was performed using ethyl acetate. The organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform), thereby obtaining 2.9 g of methyl 4-[3-(4-aminophenyl)propyl]benzoate.

Workup

  1. customAfter hydrogen (3 atm) purging
  2. customwas performed at room temperature
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue under ice cooling
  6. extractionextraction
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-bde856cce062422abdd218557db6d04c
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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