HCID 57054047, compound → HCID 28894641, compound

HRID 1508785Notes

Reaction equation

HRID 1508785 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[C:3]([NH2:5])=[O:4]>[Pd].C(OCC)(=O)C.CO>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([N:2]([CH3:1])[C:3]([NH2:5])=[O:4])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 57054047HCID 57054047, compound

Product 1

HCID 28894641HCID 28894641, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A 100-mL round bottom flask was charged with 1-methyl-1-(4-nitrophenyl)urea (0.63 g, 3.26 mmol) and 10% palladium on carbon (0.15 g) in 1:1 ethyl acetate/methanol (20 mL). This mixture was vigorously stirred under H2 (1 atm) for 5 h. After this time, the mixture was filtered through celite to afford the title compound (0.54 g, 100%) as a white solid. MW=165.19. 1H NMR (DMSO-d6, 500 MHz) δ 6.90-6.86 (m, 2H), 6.57-6.53 (m, 2H), 5.29 (br s, 2H), 5.11 (s, 2H), 3.00 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-3218ee0a6cc44141b4bd805b14f2d31b
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…