3-Hydroxybenzaldehyde → 2-(3-formylphenoxy)acetamide
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethis was heated
- temperatureAfter cooled to room temperature
- filtrationinsolubles were filtered
- concentrationthe filtrate was concentrated under reduced pressure
- dissolutionThe resulting residue was dissolved in tetrahydrofuran
- temperatureby heating
- filtrationInsolubles were filtered
- concentrationconcentration under reduced pressure
- washThe resulting crude crystals were washed with a mixed solution of tetrahydrofuran and t-butyl methyl ether
- customdried
Sources & evidence
- ORD record
- ord-b4107373002b473c9a38936866d0342a
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989478B2
Reaction notes
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