5-Nitro-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)-pyridine → 6-(2,2,6,6-Tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-ylamine

HRID 456004Notes

Reaction equation

HRID 456004 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:11][C:12]([CH3:19])([CH3:18])[O:13][C:14]([CH3:17])([CH3:16])[CH:15]=2)=[N:8][CH:9]=1)([O-])=O.[H][H]>CCO.[Pd]>[CH3:18][C:12]1([CH3:19])[CH2:11][CH:10]([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:15][C:14]([CH3:17])([CH3:16])[O:13]1

Participants

5

Reactant 2

HCID 576665155-Nitro-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)-pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 576665556-(2,2,6,6-Tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-ylamineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-nitro-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)-pyridine (as prepared in the previous step, 15.0 g, 57.1 mmol) in EtOH (60 mL) was added 10% Pd/C (7.00 g). The resulting mixture was hydrogenated at 50 psi of hydrogen pressure for 2 h. The reaction mixture was filtered through a pad of Celite and concentrated in vacuo to obtain a beige solid (12.7 g, 95%) which was directly used in next step without further purification. 1H-NMR (CDCl3; 400 MHz): δ 8.05 (br s, 1H), 6.98 (m, 2H), 3.59 (br s, 2H), 3.16 (m, 1H), 1.79 (m, 2H), 1.52 (m, 2H), 1.35 (s, 6H), 1.26 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C14H22N2O, 235.2 (M+H), found 235.1.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b34b291078f341eca9e8205987e4c56a
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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