Nitric Acid → 2-Carboxy-3-methyl-5-nitrothiophene

HRID 844163Notes

Reaction equation

HRID 844163 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[CH3:9])([OH:3])=[O:2].[N+:10]([O-])([OH:12])=[O:11].C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[C:1]([C:4]1[S:5][C:6]([N+:10]([O-:12])=[O:11])=[CH:7][C:8]=1[CH3:9])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 902693-Methyl-2-thenoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 183769572-Carboxy-3-methyl-5-nitrothiopheneYield 53%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-carboxy-3-methylthiophene (10 g, 70.3 mmol) in 80 mL of trifluoroacetic acid at 0° C. was added HNO3 (1.2 mL,1.0 eq.) dropwise. The reaction mixture was warmed to ambient temperature and after 4 hours another 1.0 eq. of HNO3 was added. The reaction mixture was made basic with aqueous sodium bicarbonate and washed with ethyl acetate. The aqueous layer was acidified with concentrated HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 5.75 g (53%) of 2-carboxy-3-methyl-5-nitrothiophene and 2-carboxy-3-methyl-4-nitrothiophene, as a yellow solid.

Workup

  1. additionwas added
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc737adc7dc448e598b6371f8d8d050a
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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