3-Hydroxybenzaldehyde → 2-(3-formylphenoxy)acetamide

HRID 639726Notes

Reaction equation

HRID 639726 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Cl[CH2:11][C:12]([NH2:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:14][C:12]([CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])=[O:13]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 6580ChloroacetamideHCID 11430Potassium Carbonate

Product 1

HCID 110844662-(3-formylphenoxy)acetamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 12.21 g of 3-hydroxybenzaldehyde, 14.00 g of 2-chloroacetamide and 60 ml of dimethylformamide was added 20.70 g of potassium carbonate, and this was heated to stir at 90° C. for 2 hours. After cooled to room temperature, insolubles were filtered and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran by heating. Insolubles were filtered and the filtrate was concentration under reduced pressure. The resulting crude crystals were washed with a mixed solution of tetrahydrofuran and t-butyl methyl ether and dried to obtain 13.05 g of 3-(aminocarbonylmethoxy)benzaldehyde [Compound No. (n)] as a crystal.

Workup

  1. temperaturethis was heated
  2. temperatureAfter cooled to room temperature
  3. filtrationinsolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in tetrahydrofuran
  6. temperatureby heating
  7. filtrationInsolubles were filtered
  8. concentrationconcentration under reduced pressure
  9. washThe resulting crude crystals were washed with a mixed solution of tetrahydrofuran and t-butyl methyl ether
  10. customdried

Sources & evidence

ORD record
ord-6644c46d1a3542499f32cf5648ae6866
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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