Pyridine → 2-(2-Hydroxy-3-(1-naphthyloxy)propyl)-1H-isoindole-1,3(2H)-dione

HRID 1904392ノート

反応式

HRID 1904392 の反応式
CC(CC([C:7]1[C:12](O)=[CH:11][C:10]([OH:14])=[C:9]([CH2:15][CH:16]=[C:17]([CH3:19])C)[C:8]=1[O-])=O)C.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.C1(=O)NC(=[O:37])C2=CC=CC=C12.[K].N1C=C[CH:47]=[CH:46][CH:45]=1>C(O)CCC.C(Cl)(Cl)Cl.CO.C(O)(=O)C>[C:10]1([O:14][CH2:45][CH:46]([OH:37])[CH2:47][N:25]2[C:21](=[O:31])[C:22]3=[CH:30][CH:29]=[CH:28][CH:27]=[C:23]3[C:24]2=[O:26])[C:9]2[C:8](=[CH:19][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 6809PhthalimideHCID 24194345Phthalimide potassium saltHCID 252006104-Prenylphlorisovalerophenone

生成物 1

HCID 3822052-(2-Hydroxy-3-(1-naphthyloxy)propyl)-1H-isoindole-1,3(2H)-dione

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 21866353chloroform methanol HOAc溶媒

実験手順

Compound X (R=1-naphthyl; 45.6 g, 0.20 mol) and phthalimide (29.4 g. 0.20 mol) were mixed in 80 ml n-butanol. To this was added a catalytic amount of potassium phthalimide (0.10 g) and pyridine (1 ml) and the mixture refluxed for 16 hr. Upon cooling, the mixture crystallized to a solid mass which was filtered and washed with chloroform and ether. The light brown solid was boiled in 400 ml ethanol and filtered hot. The insoluble tan material was identified by thin layer chromatography to be almost pure product. Upon cooling more product crystallized from the filtrate. These crops were combined and recrystallized from ethanol to give 21 g of light tan crystals that were homogenous by thin layer chromatography (95:5:3 chloroform/methanol/acetic acid, Rf =0.65) m.p. 152°-154° C.

後処理

  1. temperaturethe mixture refluxed for 16 hr
  2. temperatureUpon cooling
  3. customthe mixture crystallized to a solid mass which
  4. filtrationwas filtered
  5. washwashed with chloroform and ether
  6. filtrationfiltered hot
  7. temperatureUpon cooling more product
  8. customcrystallized from the filtrate
  9. customrecrystallized from ethanol
  10. customto give 21 g of light tan crystals that

出典と根拠

ORDレコード
ord-95c469ec60d64714a376040ee3e285e2
出典データセット
uspto-grants-1989_06
特許番号
US04837305

反応ノート

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