Triethylamine → 3-(5,6,7,8-Tetrahydroquinol-8-yl)propylamino-3-nitro-5-(pyrid-3-ylmethyl)pyridine

HRID 34921

Reaction equation

HRID 34921 reaction equation
[N:1]1[C:10]2[CH:9]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[CH:19][N:18]=1.C(N(CC)CC)C>C(O)C>[N:1]1[C:10]2[CH:9]([CH2:11][CH2:12][CH2:13][NH:14][C:17]3[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:19][N:18]=3)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 198517793-(5,6,7,8-Tetrahydroquinol-8-yl)propylamineHCID 198517872-Chloro-3-nitro-5-(pyrid-3-ylmethyl)pyridine hydrochloride

Product 1

HCID 198517973-(5,6,7,8-Tetrahydroquinol-8-yl)propylamino-3-nitro-5-(pyrid-3-ylmethyl)pyridineYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine (4.5 g), 2-chloro-3-nitro-5-(pyrid-3-ylmethyl)pyridine hydrochloride (5 g) and triethylamine (10 ml) was refluxed in ethanol (200 ml) for 7.5 hours. The solvent was removed in vacuo, the residue was dissolved in chloroform and chromatographed on silica in chloroform and later chloroform/methanol 4:1. The fractions containing the product were concentrated to give the title compound as an oil (6.1 g).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. customchromatographed on silica in chloroform and later chloroform/methanol 4:1
  4. additionThe fractions containing the product
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-4bfa4c33e2054304a26c369a1db80481
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Linked notes

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