HCID 178476798, compound → HCID 178476797, compound

HRID 511229Notes

Reaction equation

HRID 511229 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[CH2:6][CH2:7][PH:8](=[O:12])[O:9][CH2:10][CH3:11]>C(O)C.[Pd]>[NH2:16][C:15]1[CH:14]=[CH:13][C:5]([CH2:6][CH2:7][PH:8](=[O:12])[O:9][CH2:10][CH3:11])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 178476798HCID 178476798, compound

Product 1

HCID 178476797HCID 178476797, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl (3-methoxy-4-nitrobenzyl)methylphosphinate (0.64 g, 2.34 mmol) in ethanol (5.0 mL) was charged with palladium 10% wt on activated carbon (0.25 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 and the filtrate concentrated in vacuo to afford 0.54 g of ethyl (4-amino-3-methoxybenzyl)methylphosphinate (yield: 95% yield). This material was used in successive reactions without further purification. MS (ES+): m/z 244.01 [MH+] (ZQ3, polar 5 min).

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 concentrated in vacuo

Sources & evidence

ORD record
ord-18e417af5b194b5098d0909632a19795
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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