HCID 21692437, compound → HCID 90112036, compound

HRID 1508775Notes

Reaction equation

HRID 1508775 reaction equation
[CH3:1][C:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)([C:6]([NH2:8])=[O:7])[C:3]([NH2:5])=[O:4]>[Pd].C(OCC)(=O)C.C(O)C>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:2]([CH3:1])([C:3]([NH2:5])=[O:4])[C:6]([NH2:8])=[O:7])=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 21692437HCID 21692437, compound

Product 1

HCID 90112036HCID 90112036, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A 250-mL round bottom flask was charged with 2-methyl-2-(4-nitrobenzyl)malonamide (0.69 g, 2.74 mmol) and 10% palladium on carbon (0.17 g) in 1:2 ethyl acetate/ethanol (30 mL). This mixture was vigorously stirred under H2 (1 atm) for 6 h. The mixture was then filtered through celite to afford the title compound (0.28 g, 46%) as an off-white solid. MW=221.26. 1H NMR (DMSO-d6, 300 MHz) δ 7.15 (s, 2H), 7.08 (s, 2H), 6.80 (d, J=8.1 Hz, 2H), 6.41 (d, J=8.1 Hz, 2H), 4.87 (s, 2H), 2.86 (s, 2H), 1.07 (s, 3H).

Workup

  1. filtrationThe mixture was then filtered through celite

Sources & evidence

ORD record
ord-c4b41855709f4af09f007b1ed781fe4c
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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