Ethyl nitroacetate → HCID 14994411, compound

HRID 893847Notes

Reaction equation

HRID 893847 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6]NC(C)C)[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.[N+:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([O-:17])=[O:16]>C1(C)C(C)=CC=CC=1>[CH2:22]([O:21][C:19](=[O:20])[CH:18]([N+:15]([O-:17])=[O:16])[CH2:6][C:4]1[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[S:1][CH:5]=1)[CH3:23]

Participants

4

Reactant 2

HCID 69379Ethyl nitroacetateHCID 14994410HCID 14994410, compound

Product 1

HCID 14994411HCID 14994411, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

In 50 ml of dry xylene were dissolved 10.97 g of (benzo[b]thiophen-3-ylmethyl)isopropylamine and 13.3 g of ethyl nitroacetate and the temperature of the solution was raised to 100° C. with stirring under nitrogen gas stream. After 5 hours. insoluble matter was filtered off, the solvent was distilled off under reduced pressure from the filtrate, and the residue was dissolved in 500 ml of ethyl acetate. The solution was washed thrice with 100 ml of an aqueous 5% citric acid solution, thrice with 100 ml of an aqueous 5% sodium hydrogencarbonate solution, and then twice with 100 ml of a saturated aqueous sodium chloride solution and after drying with sodium sulfate, ethyl acetate was distilled off under reduced pressure from the solution. After removing excess ethyl nitroacetate by means of a vacuum pump, the residue was subjected to silica gel column chromatography to provide 11.17 g (yield of 80%) of 3-(benzo[b]thiophen-3-yl)-2-nitropropionic acid ethyl ester.

Workup

  1. filtrationinsoluble matter was filtered off
  2. distillationthe solvent was distilled off under reduced pressure from the filtrate
  3. dissolutionthe residue was dissolved in 500 ml of ethyl acetate
  4. washThe solution was washed thrice with 100 ml of an aqueous 5% citric acid solution, thrice with 100 ml of an aqueous 5% sodium hydrogencarbonate solution
  5. dry with materialtwice with 100 ml of a saturated aqueous sodium chloride solution and after drying with sodium sulfate, ethyl acetate
  6. distillationwas distilled off under reduced pressure from the solution
  7. customAfter removing excess ethyl nitroacetate by means of a vacuum pump

Sources & evidence

ORD record
ord-a388edb1447d45189c322fc42cd3574b
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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