HCID 66885651, compound → HCID 66885838, compound

HRID 604868Notes

Reaction equation

HRID 604868 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

650 mg (2.84 mmol) 2-(4-methyl-imidazol-1-yl)-5-nitro-benzonitrile dissolved in ethyl acetate (10 ml) were hydrated under an atmosphere of hydrogen at room temperature for 5 hours in the presence of 150 mg of 10% palladium on charcoal. The catalyst was filtered off and washed with ethyl acetate. The solvent of the filtrate was evaporated under reduced pressure and dried to yield 450 mg (80%) 5-amino-2-(4-methyl-imidazol-1-yl)-benzonitrile as a yellow solid. MS ISP (m/e): 199.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 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-2e174bd033664b289a00d6d0396bb0eb
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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