4-Aminopyridine → HCID 19890935, compound

HRID 893633Notes

Reaction equation

HRID 893633 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.C(N(CC)CC)C.[I-].[Cl:26]C1C=CC=C[N+]=1C.[NH2:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1>ClCCl>[ClH:26].[ClH:26].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)=[O:13]

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471Triethylamine2×HCID 1670692-Chloro-1-methylpyridinium iodideHCID 19890937HCID 19890937, compound

Product 1

HCID 19890935HCID 19890935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4 g (0.0137 mol) 2-(2-picolylseleno)benzoic acid from Example 1 and 2 ml triethylamine in 40 ml dichloromethane is treated with 3.5 g (0.0137 mol) 2-chloro-1-methylpyridinium iodide and stirred at room temperature for 1 hour. Then a solution of 1.29 g (0.0137 mol) 4-aminopyridine and 2 ml triethylamine in 30 ml dichloromethane are added dropwise within 15 min and after stirring for 2 hours the reaction mixture is extracted once with 100 ml 1 N sodium hydroxide solution and twice with 100 ml portions of water. The organic phase is dried, the solvent removed and the residue taken up in 2-propanol (80 ml)/15% HCl (10 ml). After filtration the solid crude product is dissolved in 100 ml methanol and diethyl ether is added dropwise until the solution remains turbid. The crystals which then form are filtered off after 2 hours and dried.

Workup

  1. stirringafter stirring for 2 hours the reaction mixture
  2. extractionis extracted once with 100 ml 1 N sodium hydroxide solution and twice with 100 ml portions of water
  3. customThe organic phase is dried
  4. customthe solvent removed
  5. filtrationAfter filtration the solid crude product
  6. dissolutionis dissolved in 100 ml methanol
  7. additiondiethyl ether is added dropwise until the solution
  8. customThe crystals which then form
  9. filtrationare filtered off after 2 hours
  10. customdried

Sources & evidence

ORD record
ord-98f53978efd2484883f47dc9202ffe85
Source dataset
uspto-grants-1992_06
Patent number
US05126357

Reaction notes

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