HCID 20161424, compound → HCID 13219227, compound

HRID 615183Notes

Reaction equation

HRID 615183 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:8]([C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])=[C:7]([CH3:26])[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2].Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C.[Pt]>[C:1]([C:4]1[C:5]([CH3:27])=[N:6][C:7]([CH3:26])=[C:8]([C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 20161424HCID 20161424, compoundHCID 23665649Lithium perchlorate

Product 1

HCID 13219227HCID 13219227, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 10 g (27 mmols) of 2-cyanoethyl 3-acetyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-5-carboxylate in an electrolyte of 5 g of lithium perchlorate in 250 ml of acetonitrile was electrolyzed on a platinum anode at an electrode potential of +1.2 V vs. SCE. After passing through 2 Faraday equivalents, the electrolysis was stopped, the anolyte was evaporated in vacuo, the residue was taken up in a sodium bicarbonate solution and extracted several times with methylene chloride. The organic extracts were washed with water, dried over sodium sulphate and then evaporated in vacuo. The resulting oil crystallized completely, and the solid product was thoroughly stirred in petroleum ether, filtered off with suction and dried, melting point 85° C., yield: 7.5 g (75%).

Workup

  1. customthe anolyte was evaporated in vacuo
  2. extractionextracted several times with methylene chloride
  3. washThe organic extracts were washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe resulting oil crystallized completely
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-93b8139e47334427870275bccc4bb5f4
Source dataset
uspto-grants-1985_02
Patent number
US04497821

Reaction notes

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