4-Methoxybenzylamine → HCID 178490962, compound

HRID 1894968Notes

Reaction equation

HRID 1894968 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N+:3]=1[O-:11].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=1>C(O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:2]2[N+:3]([O-:11])=[CH:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 844332-Chloro-4-nitropyridine 1-oxide

Product 1

HCID 178490962HCID 178490962, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-4-nitropyridine-1-oxide (75 g, 0.43 mol) and 1-(4-methoxyphenyl)-methanamine (125 g, 0.91 mol) in ethanol (1 L) was heated at reflux for 5 h. The reaction was allowed to cool to room temperature and cooled in a freezer overnight. The resulting cold mixture was filtered. The isolated solid was further slurried in methanol (100 mL) and filtered to give N-(4-methoxybenzyl)-4-nitropyridin-2-amine 1-oxide (51.62 g, 40% yield) as an orange solid. LCMS: (FA) ES+ 276; 1H NMR (400 MHz, d6-DMSO) δ ppm 8.34 (dd, J=6.5, 0.8 Hz, 1H), 8.27 (t, J=6.7, 6.7 Hz, 1H), 7.39-7.34 (m, 1H), 7.29 (d, J=8.6 Hz, 1H), 6.89 (d, J=8.6 Hz, 1H), 4.52 (d, J=6.6 Hz, 1H), 3.70 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperaturecooled in a freezer overnight
  4. filtrationThe resulting cold mixture was filtered
  5. filtrationfiltered

Sources & evidence

ORD record
ord-39c6d8f6b1504f64b13ec11cc3d69ff8
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

Loading…