Hydrochloric Acid → (E)-methyl 2-[2-(3-formamidophenoxy)phenyl]-3-methoxypropenoate

HRID 1741879Notes

Reaction equation

HRID 1741879 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14].[CH:20]([O:22][CH3:23])=O.[H-].[Na+].Cl.[C:27](=O)([O-])[O-:28].[K+].[K+].S(OC)(OC)(=O)=O>CN(C=O)C.O>[CH:27]([NH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[CH:20]\[O:22][CH3:23])/[C:13]([O:15][CH3:16])=[O:14])=[O:28]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 7865Methyl formateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 15125767Methyl 2-(3-aminophenoxy)phenylacetate

Product 1

HCID 15125768(E)-methyl 2-[2-(3-formamidophenoxy)phenyl]-3-methoxypropenoateYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of methyl 2-(3-aminophenoxy)phenylacetate (11.54 g) and methyl formate (27.7 ml) in DMF (25 ml) was added dropwise to a stirred suspension of sodium hydride (3.25 g) in DMF (50 ml) cooled in ice to below 10° C. (effervescence). Following the addition, the reaction mixture was stirred at room temperature for 3 hours, poured into water, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. These extracts were washed with brine, dried and concentrated to give a viscous yellow oil. Potassium carbonate (12.4 g) and dimethyl sulphate (4.25 ml) were added successively to a stirred solution of this yellow oil in DMF (50 mls) and the resulting mixture was stirred at room temperature for 3 hours, poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated to give (E)-methyl 2-[2-(3-formamidophenoxy)-phenyl]-3-methoxypropenoate (13.67, 93% yield) as a clear green gum.

Workup

  1. temperaturecooled in ice to below 10° C. (effervescence)
  2. additionthe addition
  3. extractionextracted with ethyl acetate
  4. washThese extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto give a viscous yellow oil
  8. stirringthe resulting mixture was stirred at room temperature for 3 hours
  9. extractionextracted with ethyl acetate
  10. washThe extracts were washed with water
  11. customdried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-ca2a8cf37aa84e06afc570981a7d1358
Source dataset
uspto-grants-1994_08
Patent number
US05334748

Reaction notes

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