Hydrochloric Acid → Methyl 3-aminophenylacetate

HRID 1256077Notes

Reaction equation

HRID 1256077 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 526967Methyl 2-(3-nitrophenyl)acetate

Product 1

HCID 13054266Methyl 3-aminophenylacetateYield 127.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-(3-nitrophenyl)acetate (7.3 g, 0.038 mol) and Fe (6.3 g, 0.113 mol) in MeOH (200 mL) was added concentrated HCl (20 mL). Then the mixture was stirred at room temperature over night. The mixture was filtered, the solvent was concentrated and the residue was dissolved in ethyl acetate and washed with brine, dried and concentrated to give the crude product of methyl 2-(3-aminophenyl)acetate (8.0 g, yield 97%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe solvent was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6cfc11f6dfe64330a9a0250587f79d8e
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…