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

HRID 2075980Notes

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 formiate (6.64 g, 105 mmol) and 10% palladium on charcoal (0.24 g) were added and the mixture was stirred at ambient temperature for 18 hours. It was filtered through celite. The celite was washed with methanol and the filtrate was evaporated under reduced pressure to dryness. 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 the solvent was evaporated under reduced pressure to yield the title compound (3.89 g, 97%) as a yellow solid. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=7.62 (s, 1H), 7.12 (t, 1H), 7.01 (s, 1H), 6.41-6.51 (m, 2H), 5.64 (br s, 2H), 2.13 (s, 3H).

Workup

filtrationIt was filtered through celite
washThe celite was washed with methanol
customthe filtrate was evaporated under reduced pressure to dryness
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
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-6c6ae3fee23746e79df96eac87e25430
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923450B2

Reaction notes

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