Hydrochloric Acid → 5-Chloro-4-nitrothiophene-2-carboxylic acid

HRID 605316Notes

Reaction equation

HRID 605316 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([Cl:14])=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])C.[OH-].[Li+].Cl>CO.O>[Cl:14][C:8]1[S:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 56763846HCID 56763846, compound

Product 1

HCID 132055635-Chloro-4-nitrothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The product from Example 351A (1 equiv) was dissolved in a methanol/water 3/1 mixture followed by the addition of lithium hydroxide (5 equiv). The resultant solution was stirred at room temperature for 24 hours followed by the addition of 1N aqueous hydrochloric acid until the solution was a pH of 2. The mixture was then extracted with ethyl acetate, the organic extracts dried and concentrated under vacuum to provide the title product.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customthe organic extracts dried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8671b14d8ae14514951ecdd76cc41574
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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