Nitric Acid → Methyl 5-nitrothiophene-3-carboxylate

HRID 450030

Reaction equation

HRID 450030 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[N+:10]([O-])([OH:12])=[O:11].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[S:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 574151Methyl 3-thiophenecarboxylate

Product 1

HCID 2740231Methyl 5-nitrothiophene-3-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 3-thiophene carboxylic acid methyl ester (1.8 g, 12.68 mmol) in acetic acid (7.5 ml) was added a mixture of nitric acid (0.67 ml), acetic acid (7.5 ml) and acetic anhydride (4.3 ml) at 0-10° C. The reaction mixture was stirred at 40° C. for 1 hr and then poured into crushed ice. The solid was filtered, washed with cold water and dried. The compound was recrystallised using ether/hexane to give 5-nitro-thiophene-3-carboxylic acid methyl ester (1.0 g, 42%).

Workup

  1. additionpoured
  2. custominto crushed ice
  3. filtrationThe solid was filtered
  4. washwashed with cold water
  5. customdried
  6. customThe compound was recrystallised

Sources & evidence

ORD record
ord-5a4e6afa0cb94984b084eedef3055e94
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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