Pyridine → HCID 13604836, compound

HRID 1646627Notes

Reaction equation

HRID 1646627 reaction equation
[CH2:1]([NH:3]Cl)[CH3:2].N1C=CC=CC=1.[CH3:11][C@@H:12]1[C@:17]([CH2:19][C:20]2[C:26](=[O:27])[CH:25]=[CH:24][C:22](=[O:23])[CH:21]=2)([CH3:18])[C@@H:16]2[CH2:28][CH2:29][CH:30]=[C:31]([CH3:32])[C@@:15]2([CH3:33])[CH2:14][CH2:13]1>C(O)C>[CH3:2][CH2:1][NH:3][C:24]1[C:22](=[O:23])[CH:21]=[C:20]([CH2:19][C@@:17]2([CH3:18])[C@@H:16]3[CH2:28][CH2:29][CH:30]=[C:31]([CH3:32])[C@@:15]3([CH3:33])[CH2:14][CH2:13][C@@H:12]2[CH3:11])[C:26](=[O:27])[CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 72186AvaroneHCID 12815210N-Ethylhypochlorous amide

Product 1

HCID 13604836HCID 13604836, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 2.5 g of ethylamino hydrochloride and 5 ml of pyridine to a solution of 500 mg avarone in 1000 ml of 50% ethanol, and distill off the ethanol under water-jet vacuum after 20 hours. Extract the aqueous residue with dichloromethane and chromatograph the reduced dichloromethane extract using a silica gel column and dichloromethane as extraction agent. In the course of this process 3'-ethylamino and 4'-ethylamino avarone is obtained.

Workup

  1. distillationdistill off the ethanol under water-jet vacuum after 20 hours
  2. extractionExtract the aqueous residue with dichloromethane and chromatograph the reduced dichloromethane
  3. extractionextract
  4. extractionas extraction agent

Sources & evidence

ORD record
ord-e02bd6413cd0416d9e868189c019dcfd
Source dataset
uspto-grants-1993_01
Patent number
US05180748

Reaction notes

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