Diethyl Oxalate → Ethyl (4-fluoroanilino)(oxo)acetate

HRID 904049Notes

Reaction equation

HRID 904049 reaction equation
C(O[C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C(O)C>[CH3:9][CH2:8][O:7][C:5]([C:4]([NH:16][C:15]1[CH:17]=[CH:18][C:12]([F:11])=[CH:13][CH:14]=1)=[O:10])=[O:6]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 97314-Fluoroaniline

Product 1

HCID 2774365Ethyl (4-fluoroanilino)(oxo)acetateYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyloxalate (133 g) and p-fluoroaniline (100 g) were refluxed together for 2 hours, during which time the temperature dropped from 160° to 100°. The dark coloured mixture (with suspended crystalline solid) so produced was allowed to cool to 90°, and then diluted with ethanol (100 ml). After cooling overnight, the crystalline product was filtered off and washed thoroughly with cyclohexane. The white solid so obtained, was thoroughly dried to give ethyl 4'-fluorooxanilate (114 g; 60% yield), m.p. 117°-119° (with softening at 116°).

Workup

  1. additiondropped from 160° to 100°
  2. customThe dark coloured mixture (with suspended crystalline solid) so produced
  3. temperatureto cool to 90°
  4. temperatureAfter cooling overnight
  5. filtrationthe crystalline product was filtered off
  6. washwashed thoroughly with cyclohexane
  7. customThe white solid so obtained
  8. customwas thoroughly dried

Sources & evidence

ORD record
ord-33945af75d7246739ced6af8f216da9c
Source dataset
uspto-grants-1980_10
Patent number
US04230484

Reaction notes

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