Sulfuric Acid → 6-Tert-butyl-2-methoxynicotinonitrile

HRID 1919832Notes

Reaction equation

HRID 1919832 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14]C1N=CC=CC=1C#N.C(O)(=O)C(C)(C)C.OS(O)(=O)=O>[N+]([O-])([O-])=O.[Ag+]>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([O:14][CH3:13])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6417Pivalic acidHCID 2520992-Methoxypyridine-3-carbonitrileHCID 194251856-Tert-butylpyridine-3-carbonitrile

Product 1

HCID 667452296-Tert-butyl-2-methoxynicotinonitrile

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

The title compound was synthesized according to the procedure described for the synthesis of 6-tert-butylnicotinonitrile starting from 2-methoxynicotinonitrile (8.02 g, 5.98 mmol), pivalic acid (3.05 g, 39.9 mmol), AgNO3 (0.13 g, 0.78 mmol), (NH4)2S2O8 (1.78 g, 7.78 mmol) and 6 ml 10% H2SO4. Purified by normal phase chromatography using 95/5 to 90/10 heptane/ethyl acetate. (Yield: 80 mg, 7%). 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 9 H), 4.04 (s, 3 H), 6.97 (d, J=7.81 Hz, 2 H), 7.78 (d, J=7.81 Hz, 2 H).

Workup

  1. customPurified by normal phase chromatography

Sources & evidence

ORD record
ord-51ffee7a18e14f81806c078f9decd459
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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