Sodium Carbonate → 2-Aminobenzaldehyde

HRID 1597272Notes

Reaction equation

HRID 1597272 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 111012-NitrobenzaldehydeHCID 24489Sodium Dithionite

Product 1

HCID 682552-AminobenzaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 2-nitrobenzaldehyde (50 g, 0.33 mol) in tetrahydrofuran (0.33 liter) was added dropwise to an aqueous solution (1.2 liters) of sodium dithionite (230 g, 1.32 mols) and sodium carbonate (1.68 g, 1.59 mols) under ice-cooling over a period of 2 hours while maintaining the internal temperature at 10° C. or lower. After 30 minutes, the reaction solution was extracted with ethyl acetate and the extract solution was washed with water and then dried over anhydrous sodium sulfate. The organic solvent was removed by concentration under reduced pressure to obtain the desired compound (26 g, 64%) as an yellow oil.

Workup

  1. temperaturecooling over a period of 2 hours
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washthe extract solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic solvent was removed by concentration under reduced pressure

Sources & evidence

ORD record
ord-84a7e554bb934b91892248a5fc1d140c
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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