2-(3,6-dihydro-2H-pyran-4-yl)-4-nitro-pyridine → 2-(Oxan-4-yl)pyridin-4-amine

HRID 917470Notes

Reaction equation

HRID 917470 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1>O1CCCC1.C(O)(=O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 589627032-(3,6-dihydro-2H-pyran-4-yl)-4-nitro-pyridine

Product 1

HCID 589627052-(Oxan-4-yl)pyridin-4-amineYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 550 g (26.7 mmol) 2-(3,6-dihydro-2H-pyran-4-yl)-4-nitro-pyridine in 230 ml tetrahydrofuran and 5 ml glacial acetic acid was added 2.84 g of 10% palladium on charcoal and the mixture was then stirred for 16 h under an atmosphere of hydrogen at room temperature and 1.7 bar pressure. The mixture was then filtered, washing with methanol, and the filtrate concentrated in vacuo. Flash chromatography (methanol/dichloromethane/triethylamine 100/5/1) afforded 4.75 g (100%) 2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine as a light yellow oil. ES-MS m/e (%): 179 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. washwashing with methanol
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-30f3514df22d4d7385358d6ebcfd7550
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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