Sodium Hydroxide → 2-Nitro-3-thiophenecarboxaldehyde

HRID 2080017Notes

Reaction equation

HRID 2080017 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:7]=[CH:6][S:5][C:4]=1[N+:8]([O-:10])=[O:9].[OH-:12].[Na+]>C(O)=O>[N+:8]([C:4]1[S:5][CH:6]=[CH:7][C:3]=1[CH:2]=[O:12])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13837141HCID 13837141, compound

Product 1

HCID 105588712-Nitro-3-thiophenecarboxaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

3-Dichloromethyl-2-nitro-thiophene described in Preparation Example T-1 (1.54 g, 7.26 mmol) was dissolved in formic acid (10 mL), and the solution was refluxed for 24 hours under nitrogen atmosphere. An aqueous solution of 5N sodium hydroxide was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (472 mg, 3.00 mmol, 41%) was obtained as a light brown solid.

Workup

  1. temperaturethe solution was refluxed for 24 hours under nitrogen atmosphere
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-4bba1b20929e4db5ab305b46223054d1
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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