Methanol → Methyl 3-(4-aminophenyl)propanoate

HRID 1807280Notes

Reaction equation

HRID 1807280 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:17]O>>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1

Participants

4

Reactant 3

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

Product 1

HCID 417374Methyl 3-(4-aminophenyl)propanoateYield 97%

Procedure

Thionyl chloride (2.5 mL, 4.08 g, 34.3 mmol) was added to stirred anhydrous methanol (10 mL) at 0° C. After 20 mins, 3-(4-AMINOPHENYL)PROPIONIC ACID (1.7 g, 10.3 mmol, Trans World Chemicals) was added and the mixture was stirred at rt for 16 hrs. The reaction mixture was concentrated and the residue dissolved in ethyl acetate, washed with sat. NaHCO3, water, and sat. NaCl, dried over Na2SO4 and concentrated to give methyl 3-(4-aminophenyl)propanoate (1.80 g, 97%) as a light brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with sat. NaHCO3, water, and sat. NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eab1827c42f2430db8ffdad6f827863a
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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