HCID 18938024, compound → HCID 20378758, compound

HRID 2052125Notes

Reaction equation

HRID 2052125 reaction equation
[NH2:1][P:2]([NH2:16])([NH:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)=[O:3].[H][H]>[Pd].CN(C)C=O>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([NH:4][P:2]([NH2:16])([NH2:1])=[O:3])=[O:15])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 18938024HCID 18938024, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20378758HCID 20378758, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

30 g (0.12 mole) of N-[diaminophosphinyl]-4-nitrobenzamide in 800 ml of absolute alcohol was reduced using 4.0 g of 5% Pd/C containing 50% water. A hydrogen uptake of 19.9 psi. was recorded after 60 hr. (theoretical 24 psi.). Added 2000 ml of absolute alcohol and 2000 ml of dimethylformamide to dissolve. The catalyst was removed by filtration and the filtrate flash-evaporated down to 125 ml. Chilled to 0°, filtered and washed with anhydrous ethyl ether to yield 12.4 g (48%), m.p. darkens 168°-172°, softens 290°, decomposes 340°.

Workup

  1. dissolutionto dissolve
  2. customThe catalyst was removed by filtration
  3. customthe filtrate flash-evaporated down to 125 ml
  4. temperatureChilled to 0°
  5. filtrationfiltered
  6. washwashed with anhydrous ethyl ether
  7. customto yield 12.4 g (48%)
  8. customdarkens 168°-172°
  9. customsoftens 290°
  10. customdecomposes 340°

Sources & evidence

ORD record
ord-7094258e26924fdbac708b5cea09ed95
Source dataset
uspto-grants-1980_01
Patent number
US04182881

Reaction notes

Loading…