Hydrochloric Acid → 2-Ethoxy-4-aminobenzoic acid

HRID 1005925Notes

Reaction equation

HRID 1005925 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-852b7778be63425b98a64a8040d1bc8a
Source dataset
uspto-grants-2004_09
Patent number
US06787550B1

Reaction notes

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