Hydrochloric Acid → 4-(Acetylamino)-3-hydroxy-5-nitrobenzoic acid

HRID 2400184Notes

Reaction equation

HRID 2400184 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:18]([O-:20])=[O:19])[C:13]=1[NH:14][C:15](=[O:17])[CH3:16])[C:8]([OH:10])=[O:9])(=O)C.Cl>[OH-].[Na+].O>[C:15]([NH:14][C:13]1[C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[OH:4])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 4938463-Acetoxy-4-(Acetylamino)-5-Nitrobenzoic Acid

Product 1

HCID 33646654-(Acetylamino)-3-hydroxy-5-nitrobenzoic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Compound 104 (0.850 g, 3.54 mmol) was dissolved in 0.1N NaOH (80 mL), and the mixture was stirred at room temperature for 4 hours. This was acidified with concentrated HCl (2 mL), diluted with water (20 mL), and extracted with ethyl acetate (3×60 mL). The combined extracts were dried (Na2SO4) and concentrated on a rotary evaporator to give crystalline 105 (0.712 g, 98.4% yield): mp 256°-259 ° C (methanol).

Workup

  1. extractionextracted with ethyl acetate (3×60 mL)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-c2e8537b79c341edb01232df5403ced9
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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