Methanol → Methyl 3-(4-aminophenyl)propanoate

HRID 2378569Notes

Reaction equation

HRID 2378569 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:16]=[CH:15][C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1.[CH3:17]O>>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH2:11][C:12]([O:14][CH3:17])=[O:13])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate

Procedure

A solution obtained beforehand by adding thionyl chloride (6.7 ml, WAKO) dropwise to methanol (50 ml) under ice cooling and mixing them was added dropwise with a solution of 4-aminohydrocinnamic acid (9.97 g, TCI) in methanol (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 16.5 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with ethyl acetate (200 ml), and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate Int. n-1, 13.13 g).

Workup

  1. customA solution obtained
  2. additionmixing them
  3. stirringfurther stirred for 16.5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionextracted with ethyl acetate (200 ml)
  6. washthe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
  7. customThe organic layer was dried
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1915042b1b5c45658665c19321929301
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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