Potassium Hydroxide → 5-Nitro-1-benzothiophene-2-carboxylic acid

HRID 1384842Notes

Reaction equation

HRID 1384842 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[K+]>CCO.O>[N+:15]([C:13]1[CH:12]=[CH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[CH:14]=1)([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 737499Ethyl 5-nitro-1-benzothiophene-2-carboxylate

Product 1

HCID 2389395-Nitro-1-benzothiophene-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10 g (39.8×10−3 moles) 5-nitrobenzo[b]thiophen-2-carboxylic acid ethyl ester in 250 ml of EtOH and 60 ml of H2O were reacted with 3.8 g (67.8×10−3 moles) of KOH at 60° C. for 2 hours, after which the potassium salt of the product was collected by filtration. A further fraction of the product was collected on adding isopropanol to the filtrate. The salt was dissolved in water and after acidulating the solution with HCl(c), the protonated form of the acid was precipitated out. It was purified by recrystallisation in H2O/EtOH. Yield: 85%.

Workup

  1. filtrationafter which the potassium salt of the product was collected by filtration
  2. customA further fraction of the product was collected
  3. additionon adding isopropanol to the filtrate
  4. dissolutionThe salt was dissolved in water
  5. customthe protonated form of the acid was precipitated out
  6. customIt was purified by recrystallisation in H2O/EtOH

Sources & evidence

ORD record
ord-2a480e7db0ff45ca8549bc82c30e3218
Source dataset
uspto-grants-2001_07
Patent number
US06262056B1

Reaction notes

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