4,5-Difluoro-2-nitroaniline → 1,2-Diamino-4,5-difluorobenzene

HRID 1596144Notes

Reaction equation

HRID 1596144 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1>[Pd]>[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([NH2:10])[CH:3]=1

Participants

3

Reactant 1

HCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 27367551,2-Diamino-4,5-difluorobenzene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Five grams of 4,5-difluoro2-nitroaniline is hydrogenated in the presence of Pd/C to give 4,5-difluoro-1,2-phenylenediamine, which is then converted to 5,6-difuoro-2-methylbenzimidazole using the method of Example 1. A solution of 5,6-difluoro-2-methylbenzimidazole and 10 equivalents of iodoethane in DMF is stirred at 100° C. for about 5 hours. After the reaction mixture has cooled to room temperature, the product is precipitated by the addition of diethyl ether. The precipitate is collected by suction filtration, and then resuspended in water, followed by brief stirring. The solid is collected again by suction filtration and dried at 50° C. under vacuum.

Sources & evidence

ORD record
ord-014d9a61740f44dba095dddb2edb4120
Source dataset
uspto-grants-2001_09
Patent number
US06291203B1

Reaction notes

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