N-[2-(2-methoxyphenoxy)ethyl]-3-methylamino-4-nitrobenzamide → 4-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamide

HRID 412718Notes

Reaction equation

HRID 412718 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([NH:19][CH3:20])[CH:11]=1>[Pd].CO.O1CCCC1>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH2:7][CH2:6][O:5][C:4]2[CH:22]=[CH:23][CH:24]=[CH:25][C:3]=2[O:2][CH3:1])=[O:21])=[CH:11][C:12]=1[NH:19][CH3:20]

Participants

5

Reactant 1

HCID 18537981N-[2-(2-methoxyphenoxy)ethyl]-3-methylamino-4-nitrobenzamide

Product 1

HCID 185380254-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamideYield 103.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising N-[2-(2-methoxyphenoxy)ethyl]-3-methylamino-4-nitrobenzamide (3.56 g, 10.3 mmol), suspended palladium on carbon (10%, 0.5 g) in methanol (100 mL) and tetrahydrofuran (50 mL) was stirred under a hydrogen atmosphere at ambient pressure for 2.5 hours. The mixture was filtered and the solution concentrated in vacuo to provide 4-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamide (3.37 g, 100% yield) as a green foam; MS (PB-PCI) C17H21N3O3 m/e calc 315.37; found 316 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-27ecb08c89ad483ca2208b24b1e22d96
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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