HCID 66858627, compound → HCID 66859122, compound

HRID 1803179Notes

Reaction equation

HRID 1803179 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]=[C:12]1[CH3:17]>[Pd].CO>[CH3:17][C:12]1[N:11]([C:3]2[CH:4]=[CH:5][C:6]([NH2:8])=[CH:7][C:2]=2[F:1])[CH:15]=[C:14]([CH3:16])[N:13]=1

Participants

4

Reactant 1

HCID 66858627HCID 66858627, compound

Product 1

HCID 66859122HCID 66859122, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step T (2): 10% Palladium on carbon (2.99 g, 2.81 mmol) was added under an atmosphere of nitrogen to a chilled (ice-water bath) solution of 1-(2-fluoro-4-nitrophenyl)-2,4-dimethyl-1H-imidazole (6.6 g, 28.1 mmol) dissolved in methanol (150 mL). The flask was repeatedly evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 18 h under the hydrogen atmosphere. The vessel was subsequently purged with nitrogen gas. The crude reaction mixture was filtered through a short plug of diatomaceous earth (Celite®). The reaction vessel and Celite® were rinsed with fresh methanol. The combined filtrates were concentrated in vacuo. The residue was dried under high vacuum to afford 4-(2,4-dimethyl-1H-imidazol-1-yl)-3-fluoroaniline (6.02 g, quanitative yield) as a blackish/grey solid. LC-MS (M+H)+ 206.2. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.00 (t, J=8.5 Hz, 1 H), 6.60 (s, 1 H), 6.43-6.53 (m, 2 H), 3.98 (br. s., 2 H), 2.16-2.28 (m, 6 H).

Workup

  1. customThe flask was repeatedly evacuated
  2. customflushed with hydrogen gas (double balloon)
  3. waitleft
  4. customThe vessel was subsequently purged with nitrogen gas
  5. customThe crude reaction mixture
  6. filtrationwas filtered through a short plug of diatomaceous earth (Celite®)
  7. washThe reaction vessel and Celite® were rinsed with fresh methanol
  8. concentrationThe combined filtrates were concentrated in vacuo
  9. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-de42cca77aa74d38bc3fd0eccd737ba6
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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