Hydrochloric Acid → Methyl 2-(4-aminophenyl)acetate

HRID 1264343Notes

Reaction equation

HRID 1264343 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.Cl.[CH3:13]O>>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 145334-Aminophenylacetic acid

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetateYield 74%

Procedure

To a solution of 4-aminophenylacetic acid (10 g, 66.2 mmol) in methanol (150 mL) at room temperature was added HCl conc. (37% 25 mL). The mixture became yellow and was stirred overnight. The reaction mixture was then quenched with a saturated aqueous solution of NaHCO3. The methanol was evaporated under reduced pressure and the aqueous layer was extracted several times with AcOEt. The combined organic extracts were dried over (MgSO4) and evaporated. The crude residue was purified by flash chromatography using hexane/AcOEt (4:1) as solvent mixture yielding 3 as a yellow oil (9.44 g, 74%).

Workup

  1. customThe reaction mixture was then quenched with a saturated aqueous solution of NaHCO3
  2. customThe methanol was evaporated under reduced pressure
  3. extractionthe aqueous layer was extracted several times with AcOEt
  4. dry with materialThe combined organic extracts were dried over (MgSO4)
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fc502ec782894fe9b68d44ae0a611bdd
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Reaction notes

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