Hydrochloric Acid → Methyl 3-aminophenylacetate

HRID 1264342Notes

Reaction equation

HRID 1264342 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[C:13]([O-])(O)=O.[Na+]>CO>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 13054266Methyl 3-aminophenylacetateYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe aqueous phase was extracted several times with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over (MgSO4)
  4. customevaporated
  5. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-9aff6d79ec0e4966ac3855c1b72634aa
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Reaction notes

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