Sodium → 2-(3-Trifluoromethylphenyl)-3-amino-5-phenyl-2-cyclopentenone

HRID 1111065Notes

Reaction equation

HRID 1111065 reaction equation
[Na].[F:2][C:3]([F:24])([F:23])[C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][C:8]([CH:10]([CH2:17][C:18]#[N:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]>CO>[F:2][C:3]([F:23])([F:24])[C:4]1[CH:5]=[C:6]([C:7]2[C:8](=[O:9])[CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][C:18]=2[NH2:19])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 15672493HCID 15672493, compound

Product 1

HCID 156724942-(3-Trifluoromethylphenyl)-3-amino-5-phenyl-2-cyclopentenoneYield 20.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A dry 500-ml, three-neck, round-bottomed flask equipped with a mechanical stirrer, addition funnel and a reflux condenser bearing a nitrogen inlet tube was charged with 75 ml of methanol and 4.0 g of sodium. After all the sodium had reacted, a solution containing 38.4 g of [a-(3-trifluoromethyl-benzylcarbonyl)benzyl]acetonitrile in 75 ml of methanol was added rapidly dropwise while the reaction mixture was stirred at reflux. Reflux was continued for about 16 hours after which time the reaction mixture was concentrated in vacuo. The residue was dissolved in diethyl ether and washed once with 10% hydrochloric acid. The aqueous phase was back extracted (2X) with ether and the combined organic layers were dried over magnesium sulfate and concentrated to yield a red paste. The paste was triturated with ether to yield 7.8 g of the title compound as a pale yellow solid, (MP 205° to 206° C.).

Workup

  1. customA dry 500-ml, three-neck, round-bottomed flask equipped with a mechanical stirrer, addition funnel and a reflux condenser
  2. additionwas added rapidly dropwise while the reaction mixture
  3. temperatureat reflux
  4. temperatureReflux
  5. concentrationafter which time the reaction mixture was concentrated in vacuo
  6. dissolutionThe residue was dissolved in diethyl ether
  7. washwashed once with 10% hydrochloric acid
  8. extractionThe aqueous phase was back extracted (2X) with ether
  9. dry with materialthe combined organic layers were dried over magnesium sulfate
  10. concentrationconcentrated
  11. customto yield a red paste
  12. customThe paste was triturated with ether

Sources & evidence

ORD record
ord-9ed0b6e094d042e1a53dec614c7e640b
Source dataset
uspto-grants-1990_12
Patent number
US04978386

Reaction notes

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