Pyridine → HCID 382205, compound

HRID 1904392Notes

Reaction equation

HRID 1904392 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 382205HCID 382205, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 21866353chloroform methanol HOAcSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-95c469ec60d64714a376040ee3e285e2
Source dataset
uspto-grants-1989_06
Patent number
US04837305

Reaction notes

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