Sodium Hydroxide → 4-[(Methoxycarbonyl)amino]benzoic acid

HRID 1451062Notes

Reaction equation

HRID 1451062 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)=[O:4].[OH-].[Na+]>O>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 727211HCID 727211, compound

Product 1

HCID 5060544-[(Methoxycarbonyl)amino]benzoic acidYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of methyl 4-(methoxycarbonyl)aminobenzoate (1.5 g, 7.17 mmol) in 10 mL of deionized water was added 1N sodium hydroxide (7 mL, aqueous) and the mixture was heated to 60°-70° C. for 8 h. The reaction mixture was filtered and the filtrate was neutralized with 6N HCl. The precipitated solid was separated through filtration, dried in air followed by drying in a pistol at acetone reflux in vacuo to give 754 mg (54%) of the title compound as a white solid, mp 195°-196° C.

Workup

  1. temperaturethe mixture was heated to 60°-70° C. for 8 h
  2. filtrationThe reaction mixture was filtered
  3. customThe precipitated solid was separated through filtration
  4. customdried in air
  5. dry with materialby drying in a pistol at acetone
  6. temperaturereflux in vacuo

Sources & evidence

ORD record
ord-d5b0c3ab2d0f46b5abb1f979c39e48f4
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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