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

HRID 1388311ノート

反応式

HRID 1388311 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-56e3599d198c459995706538b39754c4
出典データセット
uspto-grants-1984_02
特許番号
US04431651

反応ノート

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