4-(5-Bromo-3-methyl-2-pyridinyl)butylamine → 2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-3-nitro-5-(pyrid-3-ylmethyl)pyridine

HRID 1607033

Reaction equation

HRID 1607033 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.Cl.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:18][N:17]=1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:18][N:17]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineHCID 198517872-Chloro-3-nitro-5-(pyrid-3-ylmethyl)pyridine hydrochloride

Product 1

HCID 198517932-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-3-nitro-5-(pyrid-3-ylmethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(5-bromo-3-methylpyrid-2-yl)butylamine (11.79 g) and 2-chloro-3-nitro-5-(pyrid-3-ylmethyl)-pyridine hydrochloride (4.57 g) was refluxed in ethanol (100 ml) for 8 hours. The solvent was removed in vacuo, the residue was dissolved in water (100 ml) and then extracted with chloroform (100 ml). The chloroform extract was chromatographed on silica eluted with 5% v/v methanol in chloroform followed by recrystallisation from chloroform/hexane to give the title compound as a yellow solid, m.p. 82°-84° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (100 ml)
  3. extractionextracted with chloroform (100 ml)
  4. extractionThe chloroform extract
  5. customwas chromatographed on silica
  6. washeluted with 5% v/v methanol in chloroform
  7. customfollowed by recrystallisation from chloroform/hexane

Sources & evidence

ORD record
ord-bfab609de5ad49b8aabcf0db1a4e32d6
Source dataset
uspto-grants-1989_09
Patent number
US04863933

Linked notes

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