Reaction #2006409

Reaction equation

NaHCO3

3-aminophenylacetic acid

HCl

→

1

Yield 79.0%

Methyl-3-aminophenylacetate

Yield 79.0%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Extractionthe aqueous phase was extracted several times with CH2Cl2
3. 3
   DryingThe combined organic extracts were dried over (MgSO4)
4. 4
   Otherevaporated
5. 5
   OtherThe crude mixture was purified by flash chromatography

Procedure

To a solution of 3-aminophenylacetic acid (3 g, 19.85 mmol) in methanol (50 mL) at room temperature was added HCl conc. (37%, 7.5 mL). The mixture was stirred 6 h at room temperature then treated with a saturated aqueous solution of NaHCO3. The solvent was removed under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) and evaporated. The crude mixture was purified by flash chromatography using hexane/AcOEt (1:1) yielding 1 as a yellow oil (3.06 g, 79%).

Source