Diethyl(4-nitrophenyl)phosphonate → Diethyl (4-aminophenyl)phosphonate

HRID 870131Notes

Reaction equation

HRID 870131 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C(O)=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 284865Diethyl(4-nitrophenyl)phosphonate

Product 1

HCID 273213Diethyl (4-aminophenyl)phosphonate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 284Formic AcidSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of diethyl 4-nitrophenylphosphonate (1.07 g, 4.13 mmol, 1.00 equiv), TEA (3 mL), Palladium carbon (0.025 g). This was followed by the addition of formic acid (2 mL) dropwise with stirring at room temperature. The resulting solution was heated to reflux for 3 hr. The reaction was then quenched by the addition of 5 mL of water and the solids were filtered out. The resulting filtrate was extracted with 5×10 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. This resulted in 800 mg (85%) of diethyl 4-aminophenylphosphonate as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 3 hr
  4. customThe reaction was then quenched by the addition of 5 mL of water
  5. filtrationthe solids were filtered out
  6. extractionThe resulting filtrate was extracted with 5×10 mL of dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThis resulted in 800 mg (85%) of diethyl 4-aminophenylphosphonate as a white solid

Sources & evidence

ORD record
ord-c2597576d57a499d840c58f970af2cf3
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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