Ammonia → Cgp-36216

HRID 576014Notes

Reaction equation

HRID 576014 reaction equation
N.[CH2:2]([P:4]([CH2:7][CH2:8][C:9]#[N:10])(=[O:6])[OH:5])[CH3:3].[H][H].[OH-].[Na+].S(=O)(=O)(O)O>O.[Ni].C(O)C>[CH2:2]([P:4]([CH2:7][CH2:8][CH2:9][NH2:10])(=[O:5])[OH:6])[CH3:3]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 46929271Ethyl(2-cyanoethyl)phosphinic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 9898878Cgp-36216Yield 67%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a glass autoclave, 240 g of ethanol, 68 g of ammonia, 52 g of water, 6.4 g of Raney® nickel (doped with 1.5% by weight of chromium), 54.4 g (0.37 mol) of ethyl-(2-cyanoethyl)phosphinic acid (produced as in Example 5) are reacted at 70° C. with hydrogen at 25 bar. Following a reaction time of 8 hours, the autoclave was let down, the reaction solution was filtered and the filtrate was concentrated in vacuo. The residue obtained is taken up in 150 g of water admixed with about 30 g (0.37 mol) of 50% sodium hydroxide solution and neutralized by addition of about 18.1 g (0.19 mol) of concentrated sulfuric acid, and thereafter the water is distilled off in vacuo. The residue is taken up in ethanol and filtered. The solvent of the filtrate is removed. The product is purified by chromatography to obtain 37.4 g (67% of theory) of ethyl(3-aminopropyl)phosphinic acid as colorless oil.

Workup

  1. customa reaction time of 8 hours
  2. filtrationthe reaction solution was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue obtained
  5. distillationthe water is distilled off in vacuo
  6. filtrationfiltered
  7. customThe solvent of the filtrate is removed
  8. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-91c3a90053464b3d8984a2e9f33cb3d9
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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