3-Aminopyridine → HCID 22598273, compound

HRID 1369352Notes

Reaction equation

HRID 1369352 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].N(OC(C)(C)C)=O.N[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>N1C=CC=CC=1>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]2([CH3:11])[CH3:10])[CH:21]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 10906Tert-Butyl nitriteHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 22598273HCID 22598273, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 3.90 g (38 mmol) of tert-butyl nitrite, 7.6 mg (0.0125 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II), 120 mL of pyridine and 2.35 g (25 mmol) of 3-aminopyridine at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 1.5 g of the title compound as a colorless oil in 50.8% yield. The structure is confirmed by 1Hnmr and mass spectrographic analyses.

Workup

  1. customat 70° C
  2. customThe crude product obtained
  3. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-7e2e83b2f9914d18be4d73c1caa9d966
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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