Nitric Acid → 5-nitrothiophene-3-carboxylic acid

HRID 357747Notes

Reaction equation

HRID 357747 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.S(=O)(=O)(O)O.[OH-].[Na+].[N+:16]([O-])([OH:18])=[O:17]>>[N+:16]([C:5]1[S:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1)([O-:18])=[O:17]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6918Thiophene-3-carboxylic acidHCID 14798Sodium Hydroxide

Product 1

HCID 27772675-nitrothiophene-3-carboxylic acid

Procedure

3-Thiophenecarboxylic acid (5.12 g) was added portionwise to a mixture of nitric acid (20 ml) and sulfuric acid (11.5 ml) below 5° C. The mixture was stirred at the same temperature for 30 minutes, and poured into ice water. The mixture was alkalified with 1N sodium hydroxide and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give 5-nitro-3-thiophenecarboxylic acid (4.45 g) as crystals.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-26f79421df8a440abd63a06073068c1d
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Reaction notes

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