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

HRID 1904392노트

반응식

HRID 1904392 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 21866353chloroform methanol HOAc용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95c469ec60d64714a376040ee3e285e2
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837305

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