Ethanol → HCID 21502249, compound

HRID 1288432Notes

Reaction equation

HRID 1288432 reaction equation
Cl.[CH3:2][O:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:6]=1[CH2:7][NH2:8].[OH-].[Na+].C(O)C.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23]>O>[CH3:2][O:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:6]=1[CH2:7][NH:8][CH2:23][CH2:22][C:21]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 21502247HCID 21502247, compound

Product 1

HCID 21502249HCID 21502249, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methoxymethyl-6-nitrobenzylamine hydrochloride (20.4 g., 0.114 mole) is dissolved in a minimum volume of water and the solution is made strongly basic by the addition of 10% sodium hydroxide. The clear oil which forms is extracted into two 120-ml. portions of ether. The ether is dried with 10 g. of anhydrous sodium sulfate, filtered, and finally dried over Drierite. The dried solution is filtered and evaporated, leaving a yellow oil. The oil is dissolved in 100 ml. of absolute ethanol and 11.4 g (0.114 mole) of freshly distilled ethyl acrylate is added. This solution is allowed to stand overnight and the solvent removed by distillation from a steamcone. The oily residue is dissolved in 200 ml. of dry ether, the solution is cooled in an ice bath, and treated with dry hydrogen chloride. When precipitation is complete, the solid is filtered and dissolved in 120 ml. of boiling absolute ethanol. The hydrochloride crystallizes from this solution on cooling yielding the title product. By concentrating and cooling the mother liquor, additional title product g. is obtained. ##SPC43##

Workup

  1. extractionThe clear oil which forms is extracted into two 120-ml
  2. dry with materialThe ether is dried with 10 g
  3. filtrationof anhydrous sodium sulfate, filtered
  4. dry with materialfinally dried over Drierite
  5. filtrationThe dried solution is filtered
  6. customevaporated
  7. customleaving a yellow oil
  8. dissolutionThe oil is dissolved in 100 ml
  9. customthe solvent removed by distillation from a steamcone
  10. dissolutionThe oily residue is dissolved in 200 ml
  11. temperatureof dry ether, the solution is cooled in an ice bath
  12. additiontreated with dry hydrogen chloride
  13. customWhen precipitation
  14. filtrationthe solid is filtered
  15. dissolutiondissolved in 120 ml
  16. customThe hydrochloride crystallizes from this solution
  17. temperatureon cooling

Sources & evidence

ORD record
ord-e4abd14e3eaf47a7a35ec6e471684cb8
Source dataset
uspto-grants-1976_10
Patent number
US03988340

Reaction notes

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