4H-pyran-4-one → 1-Cyclopropyl-4-pyridone

HRID 2231981Notes

Reaction equation

HRID 2231981 reaction equation
O1[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH:8]1([NH2:11])[CH2:10][CH2:9]1>CN(C)C=O>[CH:8]1([N:11]2[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 79684H-pyran-4-oneHCID 69828Cyclopropylamine

Product 1

HCID 152725471-Cyclopropyl-4-pyridoneYield 158%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

990 mg of 4H-pyran-4-on and 1.5 g of cyclopropylamine were dissolved in 15 ml of N,N-dimethylformamide, and reacted by heating in a sealed tube at 100° C. for 6 hours. The reaction mixture was concentrated to dryness, dissolved in 80 ml of chloroform and washed with 40 ml of water. The chloroform layer was concentrated to obtain 2.2 g of 1-cyclopropyl-4-pyridone.

Workup

  1. customreacted
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutiondissolved in 80 ml of chloroform
  4. washwashed with 40 ml of water
  5. concentrationThe chloroform layer was concentrated

Sources & evidence

ORD record
ord-fb5b5cfd3ba7412badc15cdf2cd92064
Source dataset
uspto-grants-1988_11
Patent number
US04785090

Reaction notes

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