Diethyl (3-methoxy-4-nitrobenzyl)phosphonate → Diethyl(4-amino-3-methoxybenzyl)phosphonate

HRID 2279702Notes

Reaction equation

HRID 2279702 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10]>C(O)C.[Pd]>[NH2:18][C:17]1[CH:16]=[CH:15][C:5]([CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 86654016Diethyl (3-methoxy-4-nitrobenzyl)phosphonate2×

Product 1

HCID 86653997Diethyl(4-amino-3-methoxybenzyl)phosphonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl (3-methoxy-4-nitrobenzyl)phosphonate (Compound 1G, 1.07 g, 3.54 mmol) in ethanol (10.0 mL) was charged with palladium 10% wt on activated carbon (0.38 g). The reaction mixture was evacuated and purged with hydrogen gas (3×) and allowed to stir under hydrogen for 16 h. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to afford the title compound as 0.78 g of an orange oil (80%). This material was used in successive reactions without further purification. MS (ESI): m/z 274.01 [M+H]+.

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen gas (3×)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4b326172426c4aac86b5839b3efca86c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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