HCID 66885651, compound → HCID 66885838, compound

HRID 1855534Notes

Reaction equation

HRID 1855534 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

0.65 g (2.84 mmol) 2-(4-methyl-imidazol-1-yl)-5-nitro-benzonitrile dissolved in ethyl acetate (10 mL) were hydrogenated under an atmosphere of hydrogen at 20° C. for 5 h 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 the title compound (0.45 g, 80%) as 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-a060cfeb82b648a586d05d87aec99f1c
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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