Sodium Bicarbonate → 2',3'-Difluoro-4'-formylacetanilide

HRID 1607191Notes

Reaction equation

HRID 1607191 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[C:5]([F:13])[C:4]=1[F:14])#N.C([O-])(O)=[O:16].[Na+]>[Ni].C(O)=O>[F:13][C:5]1[C:4]([F:14])=[C:3]([CH:1]=[O:16])[CH:12]=[CH:11][C:6]=1[NH:7][C:8](=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 146210394'-Cyano-2',3'-difluoroacetanilide

Product 1

HCID 146210402',3'-Difluoro-4'-formylacetanilideYield 92.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent2×

Procedure

A mixture of 11 g of Raney nickel, 8.2 g of 4'-cyano-2',3'-difluoroacetanilide and 125 mL of 95% HCOOH is stirred and heated 30 minutes at 80°-85° C. The hot solution is filtered through diatomaceous earth and the cake washed with 3×100 mL of CH2CL2. The filtrate and wash are evaporated in vacuo to furnish a white solid. Excess saturated NaHCO3 is added to neutralize the residual HCOOH and the product is extracted with 3×400 mL of CH2Cl2. The CH2Cl2 extract is washed with saturated NaHCO3 and H2O (100 mL each), dried with Na2SO4 and evaporated to furnish 7.7 g (92.5% yield) of 2',3'-difluoro-4'-formylacetanilide, m.p. 154° C. The mass spectrum shows an ion at 200.

Workup

  1. temperatureheated 30 minutes at 80°-85° C
  2. filtrationThe hot solution is filtered through diatomaceous earth
  3. washthe cake washed with 3×100 mL of CH2CL2
  4. washThe filtrate and wash
  5. customare evaporated in vacuo
  6. customto furnish a white solid
  7. extractionthe product is extracted with 3×400 mL of CH2Cl2
  8. extractionThe CH2Cl2 extract
  9. washis washed with saturated NaHCO3 and H2O (100 mL each)
  10. dry with materialdried with Na2SO4
  11. customevaporated

Sources & evidence

ORD record
ord-1f1ae3f2f7f1464180de9126c4f03cc1
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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