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

HRID 1451074Notes

Reaction equation

HRID 1451074 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.S(=O)(=O)(O)O.[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:17])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 145334-Aminophenylacetic acid

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetateYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-aminophenylacetic acid (Aldrich, 5 g, 33 mmol) in 50 mL of anhydrous methanol was added 2.5 mL of concentrated sulfuric acid cautiously. The mixture was heated to reflux for 4 h. The reaction was cooled to room temperature and neutralized with sodium carbonate. The volatiles were evaporated on a rotoevaporator and the residue triturated with chloroform (80 mL) and saturated sodium bicarbonate (100 mL). The chloroform layer was separated and filtered through a small pack of silica gel. The solvent was evaporated and the residue purified through vacuum distillation at 130°-150° C. to give 2.7 g (50%) of methyl 4-aminophenylacetate as a light brown syrup.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. customThe volatiles were evaporated on a rotoevaporator
  4. customthe residue triturated with chloroform (80 mL) and saturated sodium bicarbonate (100 mL)
  5. customThe chloroform layer was separated
  6. filtrationfiltered through a small pack of silica gel
  7. customThe solvent was evaporated
  8. distillationthe residue purified through vacuum distillation at 130°-150° C.

Sources & evidence

ORD record
ord-4dfd5b88ba2b4e40a3f093ed0ba72795
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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