HCID 66885651, compound → HCID 66885838, compound

HRID 2076011Notes

Reaction equation

HRID 2076011 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:8]=2[C:9]#[N:10])[CH:6]=1>C(OCC)(=O)C.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

4

Reactant 1

HCID 66885651HCID 66885651, compound

Product 1

HCID 66885838HCID 66885838, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Methyl-imidazol-1-yl)-5-nitro-benzonitrile (650 mg, 2.84 mmol) dissolved in ethyl acetate (10 mL) was hydrogenated under an atmosphere of hydrogen at room temperature for 5 hours in the presence of 10% palladium on charcoal (150 mg). The catalyst was filtered off and washed with ethyl acetate. The solvent of the filtrate was evaporated under reduced pressure and dried to yield the title compound (450 mg, 80%) as a yellow solid. MS ISP (m/e): 199.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=7.72 (s, 1H), 7.23 (d, 1H), 7.10 (s, 1H), 6.96 (s, 1H), 6.91 (d, 1H), 2.15 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvent of the filtrate was evaporated under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-4f866d0b289042e9b0d910705819abca
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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