3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 15157376, compound

HRID 2051435Notes

Reaction equation

HRID 2051435 reaction equation
[CH3:1][CH:2]([C:5]1[C:17]([OH:18])=[C:16]2[C:8]([CH:9]3[CH:14]([CH:15]2[NH:19][CH3:20])[CH2:13][CH2:12][CH2:11][CH2:10]3)=[C:7]([CH3:21])[CH:6]=1)[CH:3]=[CH2:4].Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1>N1C=CC=CC=1>[CH3:1][CH:2]([C:5]1[C:17]([OH:18])=[C:16]2[C:8]([CH:9]3[CH:14]([CH:15]2[N:19]([CH3:20])[C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=2)[CH2:13][CH2:12][CH2:11][CH2:10]3)=[C:7]([CH3:21])[CH:6]=1)[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 15157264HCID 15157264, compound

Product 1

HCID 15157376HCID 15157376, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1.5 ml of pyridine were added 1.0 g of 7-(1-methyl-2-propenyl)-8-hydroxy-5-methyl-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene and 0.7 g of nicotinoylchloride hydrochloride, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated and then extracted with chloroform. The chloroform layer was washed with water, dried with sodium sulfate and then concentrated. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate) and then recrystallized from ethyl acetate-n-hexane to obtain 0.7 g of 7-(1-methyl-2-propenyl)-8-hydroxy-5-methyl-9-(N-methyl-N-nicotinoylamino)- 1,2,3,4,4a,9a-hexahydrofluorene having a melting point of 183°-184° C. and of colorless powdery crystal.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate)
  7. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-07a7f782288a49af8a9354a0bb5cca9b
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

Loading…