Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate → Ethyl-alpha-carbethoxy-4-methylamino-2-nitrocinnamate

HRID 637758Notes

Reaction equation

HRID 637758 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13](C)[CH3:14])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH3:2].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:24])[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 14365894Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamateHCID 178418268HCID 178418268, compound

Product 1

HCID 53938328Ethyl-alpha-carbethoxy-4-methylamino-2-nitrocinnamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The cinnamic ester (1) (5.0 g, 14.8 mmol) was dissolved in 100 mL of acetic acid and 7.6 g (17.2 mmol) of lead tetracetate was added. After allowing the mixture to stir for one hour at room temperature, the solvent was removed. Toluene (100 mL) was added and the slurry concentrated, then 100 mL of chloroform (CHCl3) was added, the solid broken up thoroughly, and the solution decanted. Chloroform (100 mL) was added to the solid and the mixture refluxed briefly, filtered, and the filtrate combined with the previous CHCl3 solution. After concentrating the organic solution the residue was chromatographed on 350 g of silica gel eluting with 1:19 (v/v) acetone:CHCl3. Fractions 83-140 (15 mL/fraction) were combined and concentrated to yield the product which was crystallized from CH2Cl2 (3.45 g, 72%), m.p. 113°-114° C.

Workup

  1. customthe solvent was removed
  2. additionToluene (100 mL) was added
  3. concentrationthe slurry concentrated
  4. addition100 mL of chloroform (CHCl3) was added
  5. customdecanted
  6. additionChloroform (100 mL) was added to the solid
  7. temperaturethe mixture refluxed briefly
  8. filtrationfiltered
  9. concentrationAfter concentrating the organic solution the residue
  10. customwas chromatographed on 350 g of silica gel eluting with 1:19 (v/v) acetone
  11. concentrationconcentrated
  12. customto yield the product which
  13. customwas crystallized from CH2Cl2 (3.45 g, 72%), m.p. 113°-114° C.

Sources & evidence

ORD record
ord-3d05e2e7dc224805b54857d2af2113ef
Source dataset
uspto-grants-1985_12
Patent number
US04558130

Reaction notes

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