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

HRID 1442525Notes

Reaction equation

HRID 1442525 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 67.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of methyl 5-methylthiophene-2-carboxylate (40.8 g, 260 mmol) in conc. sulfuric acid (400 ml) was added dropwise a solution of fuming nitric acid (16.5 ml, 391 mmol) in conc. sulfuric acid (100 ml) under ice-cooling in such a manner that the 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 poured slowly into ice (1 kg). The precipitated solid was washed with water (500 ml×6) and dried under reduced pressure to give methyl 4-nitro-5-methylthiophene-2-carboxylate (35.1 g, yield 67%).

Workup

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

Sources & evidence

ORD record
ord-fbe3460e733f43f69d1e786130daa6e3
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

Loading…