Dipropan-2-yl(4-nitrophenyl)phosphonate → Dipropan-2-yl(4-aminophenyl)phosphonate

HRID 511223Notes

Reaction equation

HRID 511223 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([P:10](=[O:19])([O:15][CH:16]([CH3:18])[CH3:17])[O:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CC(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([P:10](=[O:19])([O:11][CH:12]([CH3:14])[CH3:13])[O:15][CH:16]([CH3:18])[CH3:17])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 11572803Dipropan-2-yl(4-nitrophenyl)phosphonateHCID 178418361HCID 178418361, compound

Product 1

HCID 86653993Dipropan-2-yl(4-aminophenyl)phosphonateYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of dipropan-2-yl (4-nitrophenyl)phosphonate (287 mg, 1.0 mmol), i-PrOH (30 ml) and 10% Pd/C (30 mg) was hydrogenated under 50 psi of hydrogen pressure at 40° C. for 6 h. The reaction mixture was then filtered and the filtrate concentrated in vacuo to afford 238 mg of desired dipropan-2-yl (4-aminophenyl)phosphonate (yield: 92%), which used directly in further chemistries without purification. 1H-NMR (DMSO-d6, 400 MHz): δ=1.11 (d, J=6.0 Hz, 6 H), 1.21 (d, J=6.4 Hz, 6 H), 4.38-4.43 (m, 2 H), 5.74 (s, br, 2 H), 6.56-6.59 (m, 2 H), 7.27-7.32 (m, 2 H). MS: m/z 257.90 [MH+].

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5341f373656643af8e7cb72ba63b8e62
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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