Hydrochloric Acid → HCID 178527075, compound

HRID 1586760Notes

Reaction equation

HRID 1586760 reaction equation
[N+:1]([C:4]1[C:10]([CH2:11][P:12]([O:17]CC)([O:14]CC)=[O:13])=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl.[CH2:21]([OH:23])[CH3:22]>[Pd]>[OH:23][CH2:21][C:22]1[NH:1][C:4]2[C:10]([CH2:11][P:12]([OH:14])([OH:17])=[O:13])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 54425606HCID 54425606, compound

Product 1

HCID 178527075HCID 178527075, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-Nitro-3-(diethylphosphonomethyl)aniline (3.2 gm) in ethanol (60 mL) was combined with 10% Pd on carbon and concentrated HCl (ca. 1 mL) and hydrogenated at 55 psi for 3 hours. Additional ethanol was added and the mixture filtered through diatomaceous earth and concentrated to a solid. The solid was combined with 6N HCl and heated to reflux for 16 hours. The reaction was concentrated to a reddish solid combined with water and reconcentrated. The solid was then combined with glyoxalic acid (1.4 gm) and water (30 mL) and heated to reflux for 16 hours. The reaction mixture was concentrated to a solid. H NMR data: D2O (HDO at 4.81 ppm) 3.26 (d,2H), 4.92 (s, 2H), 7.26 (m, 3H).

Workup

  1. filtrationthe mixture filtered through diatomaceous earth
  2. concentrationconcentrated to a solid
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. concentrationThe reaction was concentrated to a reddish solid
  6. temperatureheated
  7. temperatureto reflux for 16 hours
  8. concentrationThe reaction mixture was concentrated to a solid

Sources & evidence

ORD record
ord-14c6e3a806f14cafbd085104fba0d414
Source dataset
uspto-grants-1993_06
Patent number
US05216003

Reaction notes

Loading…