Hydrochloric Acid → 4-(Acetylamino)-3-((Hydroxyacetyl)Amino)Benzoic Acid

HRID 2400191Notes

Reaction equation

HRID 2400191 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[NH:15][C:16](=[O:22])[CH2:17][O:18]C(=O)C)(=[O:3])[CH3:2].Cl>[OH-].[Na+]>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[NH:15][C:16](=[O:22])[CH2:17][OH:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10447968Methyl 4-(Acetylamino)-3-[(Acetoxyacetyl)Amino]Benzoate

Product 1

HCID 4463244-(Acetylamino)-3-((Hydroxyacetyl)Amino)Benzoic AcidYield 4.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Compound 17 (0.200 g, 0.652 mmol) was dissolved in 0.1N NaOH (7.93 mL) and stirred at room temperature for 2 hours. The alkaline aqueous layer was acidified to pH 2 with cone HCl, extracted with ethyl acetate (2×15 mL), and the extracts were dried (Na2SO4) and concentrated on a rotary evaporator to give only 8 mg of 109. The aqueous layer was concentrated on a rotary evaporator to 25% of the original volume, cooled, and the solid which separated was filtered. This was dried under vacuum to give 109 (60 mg, 58% yield) as a white solid: mp 214°-215° C.

Workup

  1. extractionextracted with ethyl acetate (2×15 mL)
  2. dry with materialthe extracts were dried (Na2SO4)
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-9aee47367f2141c591e8e28553d165c0
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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