Ammonium formate → 3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)aniline

HRID 1855350Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1.C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(2-Fluoro-4-nitro-phenyl)-4-methyl-1H-imidazole (4.66 g, 21.1 mmol) was dissolved in a mixture of methanol (25 mL) and tetrahydrofuran (100 mL). The solution was cooled to 0° C. under an atmosphere of nitrogen. Ammonium formate (6.64 g, 105 mmol) and 10% palladium on charcoal (0.24 g) was added and the mixture was stirred at 20° C. for 18 h. The mixture was filtered through celite and the celite was washed with methanol. The filtrate was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to yield the title compound (3.89 g, 97%) as a yellow solid.

Workup

filtrationThe mixture was filtered through celite
washthe celite was washed with methanol
customThe filtrate was evaporated under reduced pressure
customthe residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution
customThe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-d3e176f1b4184226be697041c33f49c3
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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