Benzonitrile → [(benzylamino)-phenylmethyl]phosphonic acid

HRID 1415489Notes

Reaction equation

HRID 1415489 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:9]([O-:16])([O:13]CC)[O:10]CC.[H][H]>[Ni]>[CH2:1]([NH:8][CH:1]([P:9](=[O:10])([OH:13])[OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7505BenzonitrileHCID 3780918DiethylphosphiteHCID 178418361HCID 178418361, compound4×

Product 1

HCID 4469578[(benzylamino)-phenylmethyl]phosphonic acid

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
60 °C

Procedure

To a solution of benzonitrile (75g; 0.73 mole) in diethyl phosphite (200g; 1.45 mole) was added W-2 Raney nickel (6g) and the whole mixture charged in an autoclave. The reactor was pressured to 600 psi with hydrogen and the mixture heated to 60° C. The pressure was maintained at 550-600 psi by addition of hydrogen as the reduction proceeded. After 18 hours, uptake of hydrogen had ceased. After cooling hydrogen was released and the catalyst filtered as the reaction product was removed from the reactor. Excess diethyl phosphite and unreacted benzonitrile was removed (135g) by distillation under reduced pressure. The residue was diethyl N-benzyl α-aminobenzylphosphonate. Hydrolysis of this residue with 18% HCl after crystallization yielded N-benzyl α-amino benzylphosphonic acid, 83g (82%), mp 233°-6°. ##STR10##

Workup

  1. additionthe whole mixture charged in an autoclave
  2. filtrationthe catalyst filtered as the reaction product
  3. customwas removed from the reactor
  4. customExcess diethyl phosphite and unreacted benzonitrile was removed (135g)
  5. distillationby distillation under reduced pressure
  6. customHydrolysis of this residue with 18% HCl
  7. customafter crystallization

Sources & evidence

ORD record
ord-96eaeba932e247cdbae1e74dfdeb8919
Source dataset
uspto-grants-1977_01
Patent number
US04005160

Reaction notes

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