2,4,6-Trimethylpyridine → HCID 18967545, compound

HRID 235145Notes

Reaction equation

HRID 235145 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13]2)=[CH:4][CH:3]=1.Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1.N1C(C)=CC(C)=CC=1C>CN(C)C=O>[N+:26]([C:25]1[C:20]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13]3)=[CH:4][CH:3]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 796132-Chloro-3-nitropyridineHCID 18967529HCID 18967529, compound

Product 1

HCID 18967545HCID 18967545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-amino-1-(1-methyl-3-piperidinyl)-naphthalene (0.252 g, 1.05 mmol from Example 61 ), 2-chloro-3-nitropyridine (0.333 g, 2.1 mmol) and collidine (0.139 mL, 1.05 mmol) in dimethylformamide (10 mL) was refluxed overnight. The reaction was concentrated at reduced pressure and the residue was taken up in methylene chloride. The organic phase was washed with 0.5N sodium hydroxide and brine, dried, concentrated onto silica gel and flash chromatographed (1×3 inches). Elution proceeded as follows: 50% ethyl acetate/hexane (500 mL) unweighed forrun; 75% ethyl acetate/hexane (400 mL) and ethyl acetate (100 mL) 0.151 g (51%) of red oil product. A sample crystallized from ether gave the title compound as red crystals. mp 107°-108° C. Analysis calculated for C21H22N4O2 ; C, 69.59; H, 6.12; N, 15.46. Found: C, 69.30; H, 5.91; N, 14.92.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction was concentrated at reduced pressure
  3. washThe organic phase was washed with 0.5N sodium hydroxide and brine
  4. customdried
  5. concentrationconcentrated onto silica gel and flash
  6. customchromatographed (1×3 inches)
  7. washElution
  8. customA sample crystallized from ether

Sources & evidence

ORD record
ord-4596cb09c7954a59b489f7cf0054e876
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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