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

HRID 2216243Notes

Reaction equation

HRID 2216243 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>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 145334-Aminophenylacetic acid

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetate

Conditions

Temperature
50 °C

Procedure

4-Aminophenylacetic acid (100 g) was suspended in methanol (1000 ml) and gaseous hydrogen chloride was passed through until the mixture was saturated. The mixture was heated at 50° C. for 2 hours and was then allowed to cool to room temperature. The solvent was evaporated in vacuo and the residue was taken up in aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to afford methyl 4-aminophenylacetate as a pale brown liquid.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-52007aae4214417a9237f1da9f2fb6bf
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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