HCID 68520592, compound → HCID 59447949, compound

HRID 1916285Notes

Reaction equation

HRID 1916285 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:17]#[N:18])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:7]=1[N+:14]([O-])=O)[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[C:7](=[CH:8][C:9]([C:12]#[N:13])=[CH:10][CH:11]=2)[NH:14][C:17]=1[NH2:18])=[O:19])[CH3:2]

Participants

4

Reactant 1

HCID 68520592HCID 68520592, compound

Product 1

HCID 59447949HCID 59447949, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

Zinc powder (2.40 g) was added portionwise to a solution of Cyano-(4-cyano-2-nitro-phenyl)-acetic acid ethyl ester (1.15 g, 4.4 mmol) in 10 mL acetic acid at 80° C. The mixture was then heated at 95° C. for 30 minutes. The reaction was then cooled to room temperature, filtered and the catalyst rinsed with acetic acid. The filtrate was concentrated to near dryness then neutralised with saturated sodium bicarbonate solution. The product was then isolated by filtration and washing with ethyl acetate to give the title compound as a tan solid (700 mg, 69%). 1H NMR (DMSO) δ 11.07 (1H, s), 7.62 (1H, d, J=8.1), 7.49 (1H, d, J=1.1), 7.33 (1H, dd, J=8.1, 1.5), 7.10 (2H, br, s), 4.24 (2H, q, J=7.3), 1.32 (3H, t, J=7.1); LC-MS (1) Rt 1.84 min; m/z 228 (ES−).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationfiltered
  3. washthe catalyst rinsed with acetic acid
  4. concentrationThe filtrate was concentrated
  5. customThe product was then isolated by filtration
  6. washwashing with ethyl acetate

Sources & evidence

ORD record
ord-6edaa91a74be42649a6858ed76b966aa
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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