Hydrochloric Acid → 2-Ethoxy-4-aminobenzoic acid

HRID 1352657Notes

Reaction equation

HRID 1352657 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([NH:14]C(=O)C)[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7])[CH3:2].Cl>[OH-].[Na+]>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6034Ethopabate

Product 1

HCID 101763852-Ethoxy-4-aminobenzoic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of methyl 2-ethoxy-4-acetamidobenzoate (50 g, 211 mmol) in aqueous solution of NaOH (15% W/W, 200 ml) was gently refluxed for 16 hours. The resulting pale brown solution was allowed to cool to room temperature and then further cooled in an ice water bath. Concentrated HCl (37% w/w) was added until the solution reached a pH of 6. The solid precipitated from the solution was filtered under vacuum, dried at 50° C. to give 38.3 g of the title compound (yield 100%).

Workup

  1. temperaturewas gently refluxed for 16 hours
  2. temperaturefurther cooled in an ice water bath
  3. customThe solid precipitated from the solution
  4. filtrationwas filtered under vacuum
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-f89630faf6d341dabf6823615714d1c1
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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