HCID 13704246, compound → HCID 59447961, compound

HRID 930188Notes

Reaction equation

HRID 930188 reaction equation
[C:1]([CH:3]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>C(O)(=O)C.[Zn]>[NH2:2][C:1]1[NH:19][C:10]2[C:9]([C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:18][CH:17]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2

Participants

4

Reactant 1

HCID 13704246HCID 13704246, compound

Product 1

HCID 59447961HCID 59447961, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

In a 500 mL round-bottom flask were added methyl 4-(1-cyano-2-ethoxy-2-oxoethyl)-3-nitrobenzoate (14.9 g, 51.0 mmol) and zinc dust (16.7 g, 255 mmol) in acetic acid (255 mL) to give a gray suspension. The addition of zinc was done over 35 minutes at room temperature over an atmosphere of nitrogen and was fairly exothermic. The mixture was heated at 100° C. for 15 hours. The mixture was allowed to cool down, filtered through Celite and rinsed with ethyl acetate. Evaporation afforded a residue which was triturated in dichloromethane-hexanes and afforded, after filtration 6.3 g of the title compound. LCMS m/z 263.2 (M+H)+, retention time (on analytical HPLC)=1.90 minutes.

Workup

  1. customto give a gray suspension
  2. temperatureto cool down
  3. filtrationfiltered through Celite
  4. washrinsed with ethyl acetate
  5. customEvaporation
  6. customafforded a residue which
  7. customwas triturated in dichloromethane-hexanes
  8. customafforded
  9. filtrationafter filtration 6.3 g of the title compound
  10. customLCMS m/z 263.2 (M+H)+, retention time (on analytical HPLC)=1.90 minutes

Sources & evidence

ORD record
ord-af71271d65a64bab99e7d7f4c29951f8
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

Loading…