Acetic Acid → Ethyl-alpha-carbethoxy-4-methylamino-2-nitrodihydrocinnamate

HRID 414699Notes

Reaction equation

HRID 414699 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:25])[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[CH3:4].C(O)(=O)C>C(O)C>[CH2:3]([O:5][C:6](=[O:25])[CH:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 53938328Ethyl-alpha-carbethoxy-4-methylamino-2-nitrocinnamate

Product 1

HCID 21280186Ethyl-alpha-carbethoxy-4-methylamino-2-nitrodihydrocinnamateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (NaBH4) (0.2 g, 5.8 mmol) was added to a slurry of the cinnamic ester (2) (3.4 g, 10.5 mmol) in 100 mL of absolute ethanol and the reaction allowed to stir at room temperature for 1.5 hours. Acetic acid (0.5 mL) was added and the mixture concentrated. The residue was dissolved in 250 mL of CHCl3 and was washed with 100 mL of saturated sodium bicarbonate (NaHCO3) solution, and H2O (100 mL). The organic phase was separated, dried (Na2SO4) and concentrated to produce 3.1 g of an orange solid. An analytical sample was obtained by crystallization from methanol(MeOH)-water, m.p. 75°-77° C.

Workup

  1. concentrationthe mixture concentrated
  2. dissolutionThe residue was dissolved in 250 mL of CHCl3
  3. washwas washed with 100 mL of saturated sodium bicarbonate (NaHCO3) solution, and H2O (100 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-29c1c848a65341189ec72c6c6ec52684
Source dataset
uspto-grants-1988_12
Patent number
US04794079

Reaction notes

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