Nitric Acid → Methyl 5-methyl-4-nitrothiophene-2-carboxylate

HRID 1442538Notes

Reaction equation

HRID 1442538 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:3]1[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[S:6][C:2]=1[CH3:1])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 580756Methyl 5-methyl-2-thiophenecarboxylate

Product 1

HCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of methyl 5-methylthiophene-2-carboxylate (109 g, 700 mmol) in conc. sulfuric acid (850 ml) was added dropwise a solution of fuming nitric acid (31 ml, 738 mmol) in conc. sulfuric acid (150 ml) under ice-cooling in such a manner that an inside temperature did not exceed 5° C. After the completion of the dropwise addition, the mixture was stirred under ice-cooling for 30 min, and slowly poured into ice (2 kg). The precipitated solid was collected by filtration, washed with water (500 ml×6) and dried under reduced pressure to give methyl 4-nitro-5-methylthiophene-2-carboxylate (62 g, yield 44%).

Workup

  1. temperaturecooling in such a manner that an inside temperature
  2. customdid not exceed 5° C
  3. additionAfter the completion of the dropwise addition
  4. temperaturecooling for 30 min
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water (500 ml×6)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-b91352552de746deaa79f3f212d952a3
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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