Hydrochloric Acid → N-[2-(2-methoxyphenoxy)ethyl]-3-methylamino-4-nitrobenzamide

HRID 412717Notes

Reaction equation

HRID 412717 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-:18])=[O:17])=[C:12](OC)[CH:11]=1.[CH3:26][NH2:27].CS(C)=O.Cl>O>[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-:18])=[O:17])=[C:12]([NH:27][CH3:26])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 6329MethylamineHCID 18537879N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamide

Product 1

HCID 18537981N-[2-(2-methoxyphenoxy)ethyl]-3-methylamino-4-nitrobenzamideYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamide (4.0 g, 11.6 mmol), aqueous methylamine (40%, 10 mL) and DMSO (2 mL) in a sealed tube was heated at 110° C. for 4 hours, cooled and then poured into water (25 mL). The dilution was treated with 3M aqueous hydrochloric acid to give an orange solid. The solid was isolated by filtration to provide N-[2-(2-methoxyphenoxy)ethyl]-3-methylamino-4-nitrobenzamide (3.56 g, 89% yield); MS (PB-PCI) C17H19N3O5 m/e calc 345.35; found 346 (MH+).

Workup

  1. temperaturecooled
  2. customto give an orange solid
  3. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-df67f7b366604eef8ebee346d09d366a
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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