Hydrochloric Acid → 4-Amino-o-anisic acid

HRID 18443

Reaction equation

HRID 18443 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[O:11][CH3:12].[Li+].[OH-].Cl>C1COCC1.O>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:13])=[O:2])=[C:5]([O:11][CH3:12])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 168705Methyl 4-amino-o-anisate

Product 1

HCID 755994-Amino-o-anisic acidYield 80%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-amino-2-methoxy benzoic acid methyl ester (5 g; 27 mmol) in THF/H2O (125 mL/25 mL) was added LiOH (4.8 g; 200 mmol) and the slurry was refluxed for 3.5 hours. The reaction mixture was neutralized using 4 M HCl (aq) and the resulting precipitate isolated by filtration and washed with H2O (2×15 mL) to give 3.26 g (80%) of an off-white solid. Mp. 144-146° C.

Workup

  1. temperaturethe slurry was refluxed for 3.5 hours
  2. customthe resulting precipitate isolated by filtration
  3. washwashed with H2O (2×15 mL)

Sources & evidence

ORD record
ord-4a58bed4de92424b8104b6c9fd88edfc
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Linked notes

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