HCID 21692446, compound → HCID 18356644, compound

HRID 1508769Notes

Reaction equation

HRID 1508769 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]([C:13]([NH2:15])=[O:14])[C:10]([NH2:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(OCC)(=O)C.C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([C:10]([NH2:12])=[O:11])[C:13]([NH2:15])=[O:14])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 21692446HCID 21692446, compound

Product 1

HCID 18356644HCID 18356644, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A 100-mL round bottom flask was charged with 2-(4-nitrobenzyl)malonamide (0.40 g, 1.68 mmol) and 10% palladium on carbon (0.10 g) in 1:2 ethyl acetate/ethanol (15 mL). This mixture was vigorously stirred under H2 (1 atm) for 56 h. After this time, the mixture was filtered through celite to afford the title compound (0.17 g, 49%) as a white solid. MW=207.23. 1H NMR (DMSO-d6, 500 MHz) δ 7.16 (s, 2H), 6.95 (s, 2H), 6.82 (d, J=8.5 Hz, 2H), 6.43 (d, J=8.5 Hz, 2H), 4.81 (s, 2H), 3.17 (t, J=8.0 Hz, 1H), 2.78 (d, J=7.5 Hz, 2H).

Workup

  1. filtrationAfter this time, the mixture was filtered through celite

Sources & evidence

ORD record
ord-49bd02d35d544f0281d7012b46d5d509
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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