Hydrochloric Acid → Methyl 3-aminophenylacetate

HRID 2402407Notes

Reaction equation

HRID 2402407 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[C:13]([O-])(O)=O.[Na+]>CO>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 13054266Methyl 3-aminophenylacetateYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-aminophenylacetic acid (3 g, 19.85 mmol) in methanol (50 mL) at room temperature was added HCl conc. (37%, 7.5 mL). The mixture was stirred 6 h at room temperature then treated with a saturated aqueous solution of NaHCO3. The solvent was removed under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) and evaporated. The crude mixture was purified by flash chromatography using hexane/AcOEt (1:1) yielding 1 as a yellow oil (3.06 g, 79%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe aqueous phase was extracted several times with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over (MgSO4)
  4. customevaporated
  5. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-6e071b3df87840dcaea40295c405bbe6
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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