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

HRID 1890523Notes

Reaction equation

HRID 1890523 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[S:10][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=1>OS(O)(=O)=O>[CH3:5][C:6]1[S:10][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

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

Product 1

HCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of concentrated HNO3 (7.2 mL, 111.5 mmol) in concentrated H2SO4 (20 mL) was added dropwise to the solution of methyl 5-methylthiophene-2-carboxylate (F-2) (13.4 g, 86.0 mmol) in concentrated H2SO4 (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 mins and poured into ice-water. The precipitate was filtered and washed with water. A solid was collected as the product (14.8 g).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customA solid was collected as the product (14.8 g)

Sources & evidence

ORD record
ord-78b05ad0cf4944c0a35c444bc876a020
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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