p-Aminoacetophenone → Ethanone, 1-[4-(2-propynylamino)phenyl]-

HRID 1722700Notes

Reaction equation

HRID 1722700 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].[CH2:11](Cl)[C:12]#[CH:13].C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:13]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)[C:12]#[CH:11]

Participants

6

Reactant 4

HCID 7468p-AminoacetophenoneHCID 122213-Chloro-1-propyneHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 11469351Ethanone, 1-[4-(2-propynylamino)phenyl]-Yield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 25 g (0.185 mol) of 4-aminoacetophenone, 12.7 ml (0.176 mol) of propargyl chloride, and 35 ml of diisopropylethylamine in 500 ml of dry toluene is stirred at 60° C. for eight hours then at 90° C. for twenty-four hours. The reaction is cooled to room temperature and poured into a saturated sodium bicarbonate solution. The organic portion is separated and concentrated in vacuo to an orange oil. The oil is chromatographed on silica gel eluting with a gradient of 20-50% ethyl acetate in hexane. The appropriate fractions are concentrated to leave a pale yellow solid. The solid is recrystallized from ethanol to give two crops of the desired product, 14.99 g (49% yield); mp 97°-100° C.

Workup

  1. waitat 90° C. for twenty-four hours
  2. temperatureThe reaction is cooled to room temperature
  3. customThe organic portion is separated
  4. concentrationconcentrated in vacuo to an orange oil
  5. customThe oil is chromatographed on silica gel eluting with a gradient of 20-50% ethyl acetate in hexane
  6. concentrationThe appropriate fractions are concentrated
  7. customto leave a pale yellow solid
  8. customThe solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-a05ca1d42dad4340929cc91936ca8f1e
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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