6-Methoxy-N-methyl-3-nitropyridin-2-amine → 6-methoxy-2-N-methylpyridine-2,3-diamine

HRID 1599304Notes

Reaction equation

HRID 1599304 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH3:10])[C:6]([N+:11]([O-])=O)=[CH:5][CH:4]=1>[Pd].O1CCOCC1>[NH2:11][C:6]1[C:7]([NH:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 1

HCID 30239146-Methoxy-N-methyl-3-nitropyridin-2-amine

Product 1

HCID 57437606-methoxy-2-N-methylpyridine-2,3-diamineYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A procedure similar to that described in Example 6 was repeated, except that 3.45 g of 6-methoxy-2-methylamino-3-nitropyridine (prepared as described in Preparation 67), 0.70 g of 10% w/w palladium-on-charcoal and 50 ml of dioxane were used, to give 2.66 g of the title compound having Rf=0.12 (on silica gel thin layer chromatography using a 1:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-86ab60f610804096b2165d22419f22c0
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

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