Propionic Acid → HCID 21993246, compound

HRID 1977537Notes

Reaction equation

HRID 1977537 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.C(O)(=O)CC.[BH4-].[Na+].[CH3:16][C:17](=O)[CH2:18][CH3:19]>>[CH:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1)([CH2:18][CH3:19])[CH3:16]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 6569Methyl Ethyl KetoneHCID 7934m-ToluidineHCID 4311764Sodium borohydride

Product 1

HCID 21993246HCID 21993246, compound

Conditions

Temperature
0 °C

Procedure

3-Toluidine (107.16 g), 2-butanone (72.11 g) and propionic acid (74.08 g) were stirred and cooled to 0° C. Sodium borohydride (37.83 g) was then added in portions keeping the temperature below 5° C. After allowing to warm to room temperature the reaction mixture was carefully poured onto ice/water. The product was extracted into ethyl acetate, washed with water, 2% hydrochloric acid and finally water again before drying over magnesium sulphate. Evaporation of the solvent under reduced pressure gave a brown oil which was purified by chromatography on silica gel.

Workup

  1. customthe temperature below 5° C
  2. temperatureto warm to room temperature the reaction mixture
  3. additionwas carefully poured onto ice/water
  4. extractionThe product was extracted into ethyl acetate
  5. washwashed with water, 2% hydrochloric acid and finally water again
  6. dry with materialbefore drying over magnesium sulphate
  7. customEvaporation of the solvent under reduced pressure
  8. customgave a brown oil which
  9. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-57533be3b7fc4339b65f080dd2f5ca8c
Source dataset
uspto-grants-2001_05
Patent number
US06235096B1

Reaction notes

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