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

HRID 1947796Notes

Reaction equation

HRID 1947796 reaction equation
[CH3:1][CH:2]([O:4][P:5]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)(=[O:10])[O:6][CH:7]([CH3:9])[CH3:8])[CH3:3].[H][H]>[Pd].CC(O)C>[CH3:9][CH:7]([O:6][P:5]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)(=[O:10])[O:4][CH:2]([CH3:1])[CH3:3])[CH3:8]

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, 6H), 1.21 (d, J=6.4 Hz, 6H), 4.38-4.43 (m, 2H), 5.74 (s, br, 2H), 6.56-6.59 (m, 2H), 7.27-7.32 (m, 2H). 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-ca1fe34df4dd441ea8bf90e06edf2f4b
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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