Dimethylformamide → HCID 53659605, compound

HRID 358844Notes

Reaction equation

HRID 358844 reaction equation
CN(C=O)C.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1I)(=[O:8])[CH3:7].[C:18]([OH:22])(=[O:21])[CH:19]=[CH2:20].C([O-])(=O)C.[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[CH:20]=[CH:19][C:18]([OH:22])=[O:21])(=[O:8])[CH3:7]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6581Acrylic AcidHCID 517045Sodium AcetateHCID 15113904HCID 15113904, compound

Product 1

HCID 53659605HCID 53659605, compoundYield 78.7%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

To a 200-ml flask were added 40 ml of DMF, 20 g (0.0717 mole) of 2-acetylamino-5-fluoroiodobenzene, 5.85 g (0.0812 mole) of acrylic acid, 7.77 g (0.0947 mole) of anhydrous sodium acetate, 10 mg of palladium chloride and 30 mg of triphenylphosphine. This mixture was stirred at 125° to 130° C. for 3 hours and poured into 200 ml of water, and then a large amount of crystal precipitated. Sodium hydroxide was added to this aqueous solution containing the crystal while stirring the solution as it was, until the pH of the solution became 9.0 to obtain a uniform solution. Thereafter, 2 g of activated carbon was added to the solution, and after stirring at room temperature for 15 minutes, the insoluble matter was filtered off. The filtrate was acidified to a pH of 4.0 with conc. hydrochloric acid, and then white crystal precipitated. This crystal was filtered off and vacuum-dried to obtain 12.6 g of 2-acetylamino-5-fluorocinnamic acid. The yield was 78.5% of the theoretical value, and the melting point was 232° to 233° C. The 1H-NMR and IR of this compound were as follows:

Workup

  1. customa large amount of crystal precipitated
  2. additionSodium hydroxide was added to this aqueous solution
  3. additioncontaining the crystal
  4. stirringwhile stirring the solution as it
  5. customto obtain a uniform solution
  6. additionThereafter, 2 g of activated carbon was added to the solution
  7. stirringafter stirring at room temperature for 15 minutes
  8. filtrationthe insoluble matter was filtered off
  9. customwhite crystal precipitated
  10. filtrationThis crystal was filtered off
  11. customvacuum-dried

Sources & evidence

ORD record
ord-4c800ce7b7be49df8bf857e956dc4620
Source dataset
uspto-grants-1991_03
Patent number
US04997972

Reaction notes

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