Water → HCID 69976476, compound

HRID 1108671Notes

Reaction equation

HRID 1108671 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4](=[CH:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH2:26][CH2:27][CH3:28].O>CN(C)C=O>[CH3:8][O:7][C:5](=[O:6])[C:4](=[CH:9][NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:15][CH:16]=1)[C:3]([O:2][CH3:1])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 69976935HCID 69976935, compound

Product 1

HCID 69976476HCID 69976476, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7 g (28 mMol) of 2-(4-Hydroxy-anilinomethylene)-propanedioic acid dimethyl ester, 3.9 g (28 mMol) of Potassium carbonate in 50 ml of dimethylformamide, 7.3 g (28 mMol) of Butyl iodide were added dropwise with stirring at room temperature. The reaction mixture was heated at 80° C. for 24 hours. Then the reaction mixture was poured into 50 ml of water and extracted three times with ethyl acetate. The organic layer was washed with a solution of sodium hydroxyde (15%) and thereafter with water, dried and evaporated and gave 4.5 g of the title compound which is a white solid melting at 46-47° C., UV 328 nm (E=685).

Workup

  1. additionwere added dropwise
  2. temperatureThe reaction mixture was heated at 80° C. for 24 hours
  3. extractionextracted three times with ethyl acetate
  4. washThe organic layer was washed with a solution of sodium hydroxyde (15%)
  5. dry with materialwith water, dried
  6. customevaporated

Sources & evidence

ORD record
ord-267951821ab346e3be79e902bd4e9de2
Source dataset
uspto-grants-2000_05
Patent number
US06069170

Reaction notes

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