HCID 136340693, compound → HCID 178509732, compound

HRID 570965Notes

Reaction equation

HRID 570965 reaction equation
[N+:1]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1/[CH:9]=[CH:10]/[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[NH:8][CH:7]=[N:6][C:5]=1/[CH:9]=[CH:10]/[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 136340693HCID 136340693, compound

Product 1

HCID 178509732HCID 178509732, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Palladium on carbon (0.5 g) was added to a solution of (E)-4-(2-(5-nitro-1H-imidazol-4-yl)vinyl)benzonitrile (10 g, 0.04 mol) in methanol (500 mL) and the resulting mixture hydrogenated at atmospheric pressure for 24 hours. The catalyst was removed by filtering through a short bed of Celite™, and the Celite™ washed with 10% MeOH/DCM (200 mL). The filtrate was evaporated to dryness and purified by column chromatography (10% MeOH/DCM) to leave the product as a yellow/brown solid (6 g, 69%). δH (DMSO-d6) 11.76 (1H, bs, NH), 7.70 (2H, d, J=8.4), 7.50 (2H, d, J=8.4), 7.44 (1H, d, J=16.0), 7.36 (1H, s), 6.42 (1H, d, J=16.0), 5.17 (2H, bs, NH2); IR (cm−1) 2220 (CEN), 1629 (C═C); MS (m/z) 211.0969 (C12H11N4 (M+1)) requires 211.0984.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through a short bed of Celite™
  3. washthe Celite™ washed with 10% MeOH/DCM (200 mL)
  4. customThe filtrate was evaporated to dryness
  5. custompurified by column chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-ac97c4f143d740c8b440cb3ebab19a45
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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