Tetramethyl 1-(4-nitrobenzyl)methylenebisphosphonate → Tetramethyl 1-(4-aminobenzyl)methylenebisphosphonate

HRID 1841904Notes

Reaction equation

HRID 1841904 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][CH:9]([P:16](=[O:21])([O:19][CH3:20])[O:17][CH3:18])[P:10](=[O:15])([O:13][CH3:14])[O:11][CH3:12])=[CH:6][CH:5]=1)([O-])=O>CCO.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([P:16](=[O:21])([O:19][CH3:20])[O:17][CH3:18])[P:10](=[O:15])([O:13][CH3:14])[O:11][CH3:12])=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 86624879Tetramethyl 1-(4-nitrobenzyl)methylenebisphosphonate

Product 1

HCID 86624881Tetramethyl 1-(4-aminobenzyl)methylenebisphosphonateYield 103.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 12 (1.01 g, 2.75 mmol) and PtO2 (0.035 g, 0.15 mmol) in EtOH (40 mL, 95%) was shaken in a PARR apparatus under 55 p.s.i of H2 for 14 hr. The catalyst was removed by filtration through glass fiber filter paper and the solvent was removed under reduced pressure to give 13 as a pale yellow solid (0.959 g, 103%) that was used without purification. 1H NMR (400 MHz, CDCl3) δ 2.62 (tt, J=6.3, 23.9, 1H), 3.12 (dt, J=6.3, 16.2, 2H), 3.70 (d, J=1.9, 6H), 3.73 (d, J=1.9, 6H), 6.61 (d, J=8.5, 2H), 7.04 (d, J=8.5, 2H).

Workup

  1. customThe catalyst was removed by filtration through glass fiber
  2. filtrationfilter paper
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3ac49df9bd814095a9402e02d1e91d07
Source dataset
uspto-grants-2015_02
Patent number
US08946144B2

Reaction notes

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