Ethyl Acetate → HCID 21540638, compound

HRID 1075726Notes

Reaction equation

HRID 1075726 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[C:6]([O:17][CH3:18])[CH:5]=1)[CH3:2].[C:19](OCC)(=O)[CH3:20]>[Pt]=O.C(O)C>[CH2:1]([N:3]1[C:4]2[CH:5]=[C:6]([O:17][CH3:18])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:8][C:9]=2[N:10]=[C:19]1[CH3:20])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 21540629HCID 21540629, compound

Product 1

HCID 21540638HCID 21540638, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 24.4g. (0.09 mole) of N-ethyl-3-methoxy-6-nitro-4-trifluoromethylaniline in 200 ml. of ethyl acetate, plus 100 ml. of ethanol, was hydrogenated in the presence of 0.2g. of platinum oxide at room temperature. The theoretical amount of hydrogen was absorbed in 19 hours of shaking at 60 psi. The catalyst was removed by filtration and the solvent evaporated at reduced pressure. The solid residue was dissolved in 200 ml. of absolute ethanol and 12.58g. (0.10 mole) of ethyl methylcarboximidate hydrochloride added. The mixture was stirred overnight at room temperature and the solvent removed at reduced pressure. Trituration of the brown residue with 200 ml. of chloroform, filtration, and evaporation of solvent from the filtrate left the crude residual product. Crystallization from hexane--CCl4 (3:1) gave 18.1g. (76%) of brown, shiny needles. Recrystallization from hexane gave the pure product, m.p. 127°-129.5°C. whose structure was confirmed by an nmr spectrum.

Workup

  1. customat room temperature
  2. customThe theoretical amount of hydrogen was absorbed in 19 hours
  3. customThe catalyst was removed by filtration
  4. customthe solvent evaporated at reduced pressure
  5. dissolutionThe solid residue was dissolved in 200 ml
  6. addition(0.10 mole) of ethyl methylcarboximidate hydrochloride added
  7. stirringThe mixture was stirred overnight at room temperature
  8. customthe solvent removed at reduced pressure
  9. filtrationof chloroform, filtration, and evaporation of solvent from the filtrate
  10. waitleft the crude residual product
  11. customCrystallization from hexane--CCl4 (3:1)
  12. customgave 18.1g
  13. customRecrystallization from hexane
  14. customgave the pure product, m.p. 127°-129.5°C. whose structure

Sources & evidence

ORD record
ord-28fc9614d78945b3b8a968e5b6aff282
Source dataset
uspto-grants-1976_05
Patent number
US03954438

Reaction notes

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