2-Cyano-1-phosphonoethanesulfonate → 3-Amino-1-phosphonopropanesulfonic Acid

HRID 2693

Reaction equation

HRID 2693 reaction equation
[C:1]([CH2:3][CH:4]([P:9]([OH:12])([OH:11])=[O:10])[S:5]([O-:8])(=[O:7])=[O:6])#[N:2].[H][H]>N.[Rh]>[NH2:2][CH2:1][CH2:3][CH:4]([P:9]([OH:12])([OH:11])=[O:10])[S:5]([OH:8])(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 867523042-Cyano-1-phosphonoethanesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 189360993-Amino-1-phosphonopropanesulfonic Acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 222AmmoniaSolvent

Procedure

The hydrogenation of 2-cyano-1-phosphonoethanesulfonate is carried out using the hydrogenation technique of Freifelder (J. Am. Chem. Soc., 82, 2386 (1960)). The cyano compound (2.15 g; 0.01 mole) is placed in 20 ml of 10% methanolic ammonia. Rhodium on alumina (5%) catalyst (0.5 g) is added, and the mixture is hydrogenated at 40 PSI on a Parr apparatus for several hours (until uptake of hydrogen is complete). The catalyst is filtered off, and the filtrate is evaporated dry. The product is purified by dissolving the residue in water, adding ethanol to give a precipitate, and collecting the solids by filtration. Further purification is accomplished by again recrystallizing from water/ethanol.

Workup

  1. waitthe mixture is hydrogenated at 40 PSI on a Parr apparatus for several hours
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customdry
  5. customThe product is purified
  6. dissolutionby dissolving the residue in water
  7. additionadding ethanol
  8. customto give a precipitate
  9. customcollecting the solids
  10. filtrationby filtration
  11. customFurther purification
  12. customby again recrystallizing from water/ethanol

Sources & evidence

ORD record
ord-8f0adc11e00943cfa52c22b2a6fa6941
Source dataset
uspto-grants-1998_03
Patent number
US05731299

Linked notes

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