Lithium iodide → 5-(4-Hydroxyphenyl)-6-methyl-3,4-dihydropyridin-2(1H)-one

HRID 1388311Notes

Reaction equation

HRID 1388311 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 132689755-(4-Methoxyphenyl)-6-methyl-3,4-dihydropyridin-2(1H)-one

Product 1

HCID 132689765-(4-Hydroxyphenyl)-6-methyl-3,4-dihydropyridin-2(1H)-oneYield 36.8%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

A mixture containing 9 g of 3,4-dihydro-5-(4-methoxyphenyl)-6-methyl-2(1H)-pyridinone, 100 ml of collidine and 38 g of lithium iodide was heated under reflux for 28 hours and then concentrated to dryness on a rotary evaporator. The residue was dissolved in 100 ml of water and again concentrated to dryness on a rotary evaporator; this process was repeated twice to remove the last traces of collidine. The solid residue was dissolved in water and the aqueous solution acidified with concentrated hydrochloric acid. The gummy solid that separated on chilling was collected, washed with water, dried at room temperature, recrystallized from ether-isopropyl alcohol using decolorizing charcoal and then chromatographed over 100 g of silica gel using 5% methanol in ether as eluant to produce 3.1 g of 3,4-dihydro-5-(4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone, m.p. 197°-200° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 28 hours
  3. concentrationconcentrated to dryness on a rotary evaporator
  4. dissolutionThe residue was dissolved in 100 ml of water
  5. concentrationagain concentrated to dryness on a rotary evaporator
  6. customto remove the last traces of collidine
  7. dissolutionThe solid residue was dissolved in water
  8. customThe gummy solid that separated
  9. temperatureon chilling
  10. customwas collected
  11. washwashed with water
  12. customdried at room temperature
  13. customrecrystallized from ether-isopropyl alcohol using
  14. customchromatographed over 100 g of silica gel using 5% methanol in ether as eluant

Sources & evidence

ORD record
ord-56e3599d198c459995706538b39754c4
Source dataset
uspto-grants-1984_02
Patent number
US04431651

Reaction notes

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