Hydrochloric Acid → [4-(Methylamino)phenyl]acetic acid

HRID 1671365Notes

Reaction equation

HRID 1671365 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15892780Methyl 2-(4-(methylamino)phenyl)acetate

Product 1

HCID 290114[4-(Methylamino)phenyl]acetic acidYield 46.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-(methylamino)phenyl)acetate (721 mg, 4.0 mmol) was dissolved in tetrahydrofuran (10 mL) and treated with a 1 M aqueous solution of lithium hydroxide (4.4 mmol). After 3 hours, the mixture was acidified with 1 N aqueous hydrochloric acid and concentrated to remove tetrahydrofuran. The aqueous phase was extracted with dichloromethane (2×20 mL) and the organic layer was dried and concentrated to give 2-(4-(methylamino)phenyl)acetic acid (309 mg, 1.87 mmol).

Workup

  1. concentrationconcentrated
  2. customto remove tetrahydrofuran
  3. extractionThe aqueous phase was extracted with dichloromethane (2×20 mL)
  4. customthe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3d87794dd954987ab11ad7c998b98c2
Source dataset
uspto-grants-2011_08
Patent number
US07994223B2

Reaction notes

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