Nitric Acid → 4-Nitrothiophene-2-carboxylic acid

HRID 440270

Reaction equation

HRID 440270 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[N+:9]([O-])([OH:11])=[O:10]>C(OC(=O)C)(=O)C.C(O)(=O)C>[N+:9]([C:4]1[CH:3]=[C:2]([C:6]([OH:8])=[O:7])[S:1][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 107002-Thiophenecarboxylic acid

Product 1

HCID 2686804-Nitrothiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

2-Thiophenecarboxylic acid (6.4 g, 50 mM) was suspended in acetic anhydride (15 ml) and fuming nitric acid (16 ml) in glacial acetic acid (25 ml) added slowly over 1 hour with stirring, while keeping the temperature of the reaction mixture below 30° C. The reaction mixture was stirred at ambient temperature for 2 hours. The product was purified by subjecting to chromatography (470 ml) on HP20SS resin using methanol/(water+1% acetic acid): 0/100→50/50 as eluant. The pure title compound was obtained (1.3 g) together with a mixture of 4- and 5- nitrothiophene-2-carboxylic acid (4.4 g).

Workup

  1. customthe temperature of the reaction mixture below 30° C
  2. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  3. customThe product was purified

Sources & evidence

ORD record
ord-6eb7bb3d44df48c598ace63eb0f97df3
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Linked notes

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