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

HRID 926020Notes

Reaction equation

HRID 926020 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.[H][H]>[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

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3918365HCID 3918365, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under an argon atmosphere, 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. Under an argon atmosphere, to the reaction mixture was added 500 mg of palladium on carbon under ice-cooling, followed by replacing with hydrogen (3 atm) at room temperature and then stirring at room temperature for 24 hours. The insoluble materials were filtered off on a celite layer and the filtrate was concentrated under reduced pressure. The residue was neutralized by the addition of a saturated aqueous sodium hydrogen carbonate solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform) to obtain 2.9 g of methyl 4-[3-(4-aminophenyl)propyl]benzoate as a pink oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationThe insoluble materials were filtered off on a celite layer
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe residue was neutralized by the addition of a saturated aqueous sodium hydrogen carbonate solution under ice-
  6. temperaturecooling
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-47cb9838ad754f28a666064f3f68f35a
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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