Stannous Chloride → 4-(4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine

HRID 1831540Notes

Reaction equation

HRID 1831540 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=2[N+:22]([O-])=O)=[C:5]([CH3:25])[CH:4]=1.Cl[Sn]Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=2[NH2:22])=[C:5]([CH3:25])[CH:4]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 22052119[4-(4-Methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine

Product 1

HCID 696581434-(4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[4-(4-Methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine (0.43 g, 0.36 mmol) and SnCl2 (0.2 g, 1.08 mmol) in ethanol (2 mL) were heated to 70° C. for 4 h. The solution was cooled to room temperature and quenched with saturated aqueous NaHCO3 then extracted with EtOAc, washed with H2O, brine, dried (Na2SO4), filtered, and concentrated in vacuo to give a crude yield of 0.40 g (99%) of 4-(4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine; MS(EI) m/z 316.28 [(M+H)+, 100]. The crude product was taken on to Part E.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionthen extracted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fcead9dbb9a40d99cee8441f4fc6cad
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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