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

HRID 916494Notes

Reaction equation

HRID 916494 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-168504d1bd3b4b0fa1ec5deb2af249f3
Source dataset
uspto-grants-2007_09
Patent number
USRE039850E1

Reaction notes

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