2-Chloro-5-nitropyridine → HCID 18967518, compound

HRID 235128Notes

Reaction equation

HRID 235128 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:23]=[CH:24][C:25](Cl)=[N:26][CH:27]=1)([O-:21])=[O:20]>CN(C)C1C=CN=CC=1.CN(C=O)C>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[N:26][CH:27]=1)([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 18967518HCID 18967518, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.212 g, 0.88 mmol), 5-nitro-2-chloropyridine (0.314 g, 1.98 mmol), and 4-dimethylaminopyridine (0.085 g, 0.7 mmol) in dry DMF (2 mL) was refluxed 8 hours. The solvent was removed in vacuo and the residue was taken up in methylene chloride. The organic phase was washed with saturated 0.5N NaOH and brine, dried over calcium sulfate and concentrated. The residue was flash chromatographed on silica gel (1×4 inches). Gradient elution with from 50% to 90% ethyl acetate/hexane gave an unweighed forerun. Continued elution with ethyl acetate gave 0.136 g of orange oil. Recrystallization from isopropanol followed by recrystallization from nitromethane gave 0.005 g (1.4%) of the title product as orange crystals: mp 121°-125° C. Analysis calculated for C20H21N5O2 ·H2O; C, 62.98; H, 6.08; N, 18.36. Found: C, 62.86; H, 5.84; N, 18.13.

Workup

  1. temperaturewas refluxed 8 hours
  2. customThe solvent was removed in vacuo
  3. washThe organic phase was washed with saturated 0.5N NaOH and brine
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel (1×4 inches)
  7. washGradient elution with from 50% to 90% ethyl acetate/hexane
  8. customgave an unweighed forerun
  9. washelution with ethyl acetate

Sources & evidence

ORD record
ord-95954f0602ab44c1a47b5e2b3b588a9f
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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