3-nitro-N-phenylpyridin-2-amine → 2-N-phenylpyridine-2,3-diamine

HRID 55526Notes

Reaction equation

HRID 55526 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.O1CCOCC1.[Pd]>[NH2:1][C:4]1[C:5]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 6117993-nitro-N-phenylpyridin-2-amine

Product 1

HCID 106790912-N-phenylpyridine-2,3-diamineYield 70.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A procedure similar to that described in Example 6 was repeated, except that 6.9 g of 3-nitro-2-phenylaminopyridine (prepared as described in Preparation 83) was hydrogenated in a mixture of 150 ml of ethanol and 50 ml of dioxane in the presence of 1.38 g of 10% w/w palladium-on-charcoal. After working up the product as described in Example 6, 4.2 g of the title compound, melting at 137°-140° C., were obtained.

Sources & evidence

ORD record
ord-cde5596a9e9c4d7bb305df229f6d5b99
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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