Sulfuric Acid → 6-Tert-butyl-4-methylnicotinonitrile

HRID 1919833Notes

Reaction equation

HRID 1919833 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]C1C(C#N)=CN=CC=1.C(O)(=O)C(C)(C)C.OS(O)(=O)=O>[N+]([O-])([O-])=O.[Ag+]>[C:1]([C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([C:9]#[N:10])=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6417Pivalic acidHCID 2278064-Methyl-3-cyanopyridineHCID 194251856-Tert-butylpyridine-3-carbonitrile

Product 1

HCID 534188646-Tert-butyl-4-methylnicotinonitrile

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 4-methylnicotinonitrile (0.5 g, 4.23 mmol), pivalic acid (2.2 g, 21.1 mmol), AgNO3 (0.09 g, 0.55 mmol), (NH4)2S2O8 (1.25 g, 5.5 mmol) and 7.5 ml 10% H2SO4. Purified by normal phase chromatography using 95/5 to 90/10 heptane/ethyl acetate. (Yield: 578 mg, 78%). 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (s, 9 H), 2.53 (s, 3 H), 7.28 (s, 1 H), 8.72 (s, 1 H).

Workup

  1. customPurified by normal phase chromatography

Sources & evidence

ORD record
ord-b3c5eaaad3d44e44a10eef4ef417fd87
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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