N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine → 4-(4-amino-2-methylphenoxy)-N1-methylbenzene-1,2-diamine

HRID 240558

Reaction equation

HRID 240558 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[CH3:19])=[CH:5][C:4]=1[N+:20]([O-])=O.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[CH:5]=[C:4]([NH2:20])[C:3]([NH:2][CH3:1])=[CH:8][CH:7]=2)=[C:11]([CH3:19])[CH:12]=1

Participants

6

Reactant 2

HCID 86650896N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamineHCID 178418361HCID 178418361, compound

Product 1

HCID 669371924-(4-amino-2-methylphenoxy)-N1-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine (1.90 g, 6.27 mmol) in ethyl acetate (10 mL) and ethanol (20 mL) was added 10% Pd/C (0.342 g, 0.321 mmol). After shaking under 50 psi of hydrogen for 1 hour, the mixture was filtered and the filtrate was concentrated under reduced pressure to provide the product as clear oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9235edec2efb4c5786933c8050ce5fc7
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Linked notes

Loading…