Acetic Acid → 2-{[3-(4-Nitrophenyl)propyl]amino}ethan-1-ol

HRID 1729281Notes

Reaction equation

HRID 1729281 reaction equation
[OH:1][CH2:2][CH2:3][N-:4][C:5](=O)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.B.[Na].C(O)(=O)C.Cl>O1CCCC1.O>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 178418435HCID 178418435, compoundHCID 178520483HCID 178520483, compound

Product 1

HCID 104211772-{[3-(4-Nitrophenyl)propyl]amino}ethan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

50 g of the previously obtained N-(2-hydroxyethyl)-3-(4-nitrophenyl)propionylamide and 31.8 g of sodium boron hydride were suspended in 500 ml of tetrahydrofuran, and 50.5 g of acetic acid was added dropwise thereto under ice cooling conditions. After completion of the addition, the solution was heated under reflux for 2 hours and then ice-cooled again, and 500 ml of water was added dropwise thereto. Afterward, 4N hydrochloric acid was added to the solution so as to adjust its pH to a level of from 5 to 6, and tetrahydrofuran was then distilled off under reduced pressure. Next, 425 ml of 4N hydrochloric acid was added to the resultant aqueous solution, and the solution was stirred at 60°-70° C. for 1 hour and then allowed to stand for cooling, so that the temperature of the solution was returned to room temperature. After washed with chloroform, the aqueous solution was adjusted to a pH of 11 by the use of a 16% aqueous sodium hydroxide solution, and extraction was carried out twice with 500 ml of chloroform. The chloroform extracts were joined and concentrated under reduced pressure, and the resultant residue was crystallized from 900 ml of toluene to obtain 38.6 g of crystalline N-(2-hydroxyethyl)-3-(4-nitrophenyl)propylamine, which had a melting point of from 82.5° to 84.5° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 2 hours
  4. temperatureice-cooled again
  5. distillationwas then distilled off under reduced pressure
  6. additionNext, 425 ml of 4N hydrochloric acid was added to the resultant aqueous solution
  7. temperaturefor cooling, so that the temperature of the solution
  8. customwas returned to room temperature
  9. washAfter washed with chloroform
  10. extractionthe aqueous solution was adjusted to a pH of 11 by the use of a 16% aqueous sodium hydroxide solution, and extraction
  11. concentrationconcentrated under reduced pressure
  12. customthe resultant residue was crystallized from 900 ml of toluene

Sources & evidence

ORD record
ord-60cf3c4818a944d6ba42c6d5d7f17669
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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