2-Aminofluorene → Propionamide, N-(2-fluoren-yl)-2-methyl-

HRID 1748961Notes

Reaction equation

HRID 1748961 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.C(N(CC)CC)C.O1CCCC1.[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29]>CCCCCC.O>[CH:3]1[C:4]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][C:2]=1[NH:1][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 15392-AminofluoreneHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 62325Isobutyryl chloride

Product 1

HCID 148890Propionamide, N-(2-fluoren-yl)-2-methyl-Yield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

In a 500 mL three-neck flask were put 15 g (83 mmol) of 2-aminofluorene, 10 g (100 mmol) of triethylamine, and 250 mL of tetrahydrofuran (THF), and the mixed solution was stirred. Then, to this mixed solution, a mixed solution of 8.8 g (83 mmol) of isobutyryl chloride and 50 mL of THF was added dropwise under cooling with ice, and the mixture was stirred at room temperature for 12 hours. After the stirring, 200 mL of water was added to this mixture, and the mixture was stirred for 1 hour. After the stirring, the precipitated solid was washed with water and subjected to suction filtration to give a white solid. A hexane suspension of this solid was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that 20 g of a white solid of N-(9H-fluoren-2-yl)isobutyramide was obtained in a yield of 97%. The synthesis scheme of Step 1 is shown in (c-1) below.

Workup

  1. customIn a 500 mL three-neck flask were put
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 1 hour
  4. washAfter the stirring, the precipitated solid was washed with water
  5. filtrationsubjected to suction filtration
  6. customto give a white solid
  7. customwas irradiated with ultrasonic waves
  8. filtrationa solid was collected by suction filtration, so that 20 g of a white solid of N-(9H-fluoren-2-yl)isobutyramide
  9. customwas obtained in a yield of 97%
  10. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-8446e5ad604f4b0299146a198865d9af
Source dataset
uspto-grants-2015_10
Patent number
US09155158B2

Reaction notes

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