4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

HRID 505924Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=2)[CH:6]=1>[Pd].C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([NH2:17])[CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=2)[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In an autoclave a suspension of 5% palladium on activated carbon (0.6 g) in 94% aqueous ethanol (200 mL) is pre-hydrogenated. After that, 4-methyl-1-(3-nitro-5-trifluoromethyl-phenyl)-1H-imidazole (6.0 g, 22.1 mmol) is added, and the mixture is hydrogenated at 70° C. and 4 bar pressure for 3 hours. Thereafter, most of the starting material is converted. The suspension is filtered over filter aid. The obtained filtrate is slowly added to water (250 mL) of 0-5° C. The resulting mixture is concentrated to a weight of 270 g, stirred, cooled to 0° C. and further stirred for almost 3 hours. The formed solid is filtered, washed with water (20 mL) and dried at 50° C. under reduced pressure to afford 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenylamine as an off-white solid. Yield: 85.8% (HPLC purity: 94 area %), Melting range: 123-124° C.

Workup

customis hydrogenated at 70° C.
filtrationThe suspension is filtered
filtrationover filter aid
additionThe obtained filtrate is slowly added to water (250 mL) of 0-5° C
concentrationThe resulting mixture is concentrated to a weight of 270 g
stirringfurther stirred for almost 3 hours
filtrationThe formed solid is filtered
washwashed with water (20 mL)
customdried at 50° C. under reduced pressure

Sources & evidence

ORD record: ord-8da38e0760304546b5702b527fa296de
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781597B2

Reaction notes

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