N-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxy-3-nitropyridin-2-amine → N2-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyridine-2,3-diamine

HRID 1943190Notes

Reaction equation

HRID 1943190 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=2)[CH2:4][O:3]1.[H][H]>O1CCOCC1.[Pd]>[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 58001746N-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxy-3-nitropyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 58001800N2-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

N-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)-3-nitro-2-pyridinamine (35.00 g, 123.6 mmol) was divided into 2 aliquots, each of which was taken up in 1,4-dioxane (500 ml) and hydrogenated over 10% Pd on carbon (paste, 1:1 w:w with water, 4.00 g) under 1 atm. hydrogen pressure, at room temperature overnight. The mixtures were filtered with suction though Celite, using an argon blanket and taking care to minimise contact of the product with air. The solution was evaporated under reduced pressure to give the title compound as a deep purple oil. This was used immediately in the next step.

Workup

  1. filtrationThe mixtures were filtered with suction though Celite
  2. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ff57f59e93184bd6a0a430608a31a735
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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