HCID 59189873, compound → HCID 59189741, compound

HRID 216612Notes

Reaction equation

HRID 216612 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]#[N:13])[C:9]([NH2:11])=[O:10])=[C:4]([N+:14]([O-])=O)[CH:3]=1>C(O)(=O)C.C1(C)C=CC=CC=1.[Zn]>[NH2:13][C:12]1[NH:14][C:4]2[C:5]([C:8]=1[C:9]([NH2:11])=[O:10])=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2

Participants

5

Reactant 1

HCID 59189873HCID 59189873, compound2×

Product 1

HCID 59189741HCID 59189741, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

2-(4-Bromo-2-nitrophenyl)-2-cyanoacetamide (Reference compound 1-1, 0.60 g, 2.1 mmol) was dissolved in acetic acid (7.0 mL) and toluene (3.5 mL), and the whole was stirred at 90° C. Zinc powder (0.97 g, 15 mmol) was added portionwise to the solution while keeping at 90° C., and then the reaction mixture was stirred at room temperature for 45 minutes. Ice-water (30 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (30 mL). The organic layer was washed with brine (30 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the mixture of the title reference compound (0.17 g) as a brown solid (yield 32%).

Workup

  1. customwhile keeping at 90° C.
  2. extractionthe whole was extracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. customto give

Sources & evidence

ORD record
ord-179b8b56d16c4fac8513fccff3b15364
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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