Phosphorus oxide (P4O10) → 1-(2-Methylphenyl)-3-(4-pyridyl)isoquinoline

HRID 464320ノート

反応式

HRID 464320 の反応式
[C:1]1([CH2:7][CH:8]([NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1C2C(=CC=CC=2)CCC1>[CH3:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:7]=[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:15]=1

参加物

4

反応物 2

HCID 14812Phosphorus oxide (P4O10)2 回HCID 13319930N-[2-phenyl-1-(4-pyridyl)ethyl]-2-methylbenzamide

生成物 1

HCID 133199311-(2-Methylphenyl)-3-(4-pyridyl)isoquinoline収率 72.1%

試薬・触媒・溶媒 1

HCID 8404Tetralin溶媒

反応条件

温度
230 °C

実験手順

37 g of N-[2-phenyl-1-(4-pyridyl)ethyl]-2-methylbenzamide in 800 ml of tetralin are heated with 240 g of phosphorus pentoxide and 60 g of Celite filtration aid, to improve distribution, at 180°-200° C. for 5 hours. After cooling to 120°-140° C., a further 120 g of phosphorus pentoxide are added and the mixture is heated at 230° C. (reflux) for 16 hours. After cooling, the tetralin is decanted off and the residue is washed several times with toluene. The washed residue is suspended in toluene and water is slowly added with stirring. The aqueous phase is separated off and made highly alkaline with potassium hydroxide. The product is extracted with toluene and, after distilling out the toluene, is chromatographed on silica gel using chloroform/ethyl acetate (8:2). 25 g of oily base are isolated, which provides a hydrochloride of melting point 255°-259° C. with ethanolic hydrochloric acid.

後処理

  1. temperatureAfter cooling to 120°-140° C.
  2. temperature(reflux) for 16 hours
  3. temperatureAfter cooling
  4. customthe tetralin is decanted off
  5. washthe residue is washed several times with toluene
  6. additionwater is slowly added
  7. customThe aqueous phase is separated off
  8. extractionThe product is extracted with toluene
  9. distillationafter distilling out the toluene
  10. customis chromatographed on silica gel

出典と根拠

ORDレコード
ord-7d9949f61041419ba6c44b1fd328cc10
出典データセット
uspto-grants-1985_10
特許番号
US04547508

反応ノート

読み込み中…