Sodium Hydroxide → 1-Phenyl-3,4-dihydroisoquinoline

HRID 499960

反応式

HRID 499960 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([CH2:21][CH2:22][NH:23][C:24](=O)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[C:25]1([C:24]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:21][CH2:22][N:23]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 95083N-Phenethylbenzamide

生成物 1

HCID 6099261-Phenyl-3,4-dihydroisoquinoline収率 97.1%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

75.5 g (532 mmol, 1.2 eq.) of P2O5 are added with stirring to a solution of 100.0 g (446 mmol) of N-(2-phenylethyl)benzamide in 375 ml of xylene. 124.1 ml (1.34 mol, 3.0 eq.) of PPCl3 are subsequently added, and the reaction mixture is refluxed with TLC monitoring. When the conversion is complete, the reaction solution is poured while hot onto ice and carefully adjusted to pH=12 using 20% NaOH. The phosphate which precipitates in the process is dissolved by addition of water. The product is subsequently extracted with toluene, converted into the hydrochloride using 1 N HCl and extracted with sufficient water. The aqueous phase is rendered basic again using 20% NaOH with ice-cooling, the reaction product is extracted with toluene, dried over MgSO4 and evaporated to dryness under reduced pressure, giving 89.7 g (432.9 mmol) of a viscous yellow oil, corresponding to 97% of theory.

後処理

  1. temperaturethe reaction mixture is refluxed with TLC monitoring
  2. additionthe reaction solution is poured while hot onto ice
  3. customThe phosphate which precipitates in the process
  4. dissolutionis dissolved by addition of water
  5. extractionThe product is subsequently extracted with toluene
  6. extractionextracted with sufficient water
  7. temperaturecooling
  8. extractionthe reaction product is extracted with toluene
  9. dry with materialdried over MgSO4
  10. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-8dd4321c9c594e5ab1f6903a3bc7459d
出典データセット
uspto-grants-2010_08
特許番号
US07767777B2

関連ノート

読み込み中…