Ethanol → 3-Amino-2-methylamino-6-phenylpyridine

HRID 356336Notes

Reaction equation

HRID 356336 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1.C(O)C>[Pd].O1CCOCC1>[NH2:9][C:8]1[C:3]([NH:2][CH3:1])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 104895752-Methylamino3-nitro-6-phenylpyridine

Product 1

HCID 108456893-Amino-2-methylamino-6-phenylpyridineYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A procedure similar to that described in Example 6 was repeated, except that 5.7 g of 2-methylamino-3-nitro-6-phenylpyridine (prepared as described in Preparation 108) were hydrogenated in 200 ml of a 1:1 by volume mixture of ethanol and 1,4-dioxane in the presence of 1.14 g of 10% w/w palladium-on-charcoal. After working up the product as described in Example 6, 4.9 g of the title compound having Rf=0.08 (on silica gel thin layer chromatography using a 1:5 by volume mixture of ethyl acetate and hexane as the developing solvent) were obtained.

Sources & evidence

ORD record
ord-fe37d8130c6a42aaa5f782c40166be23
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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