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

HRID 1919840Notes

Reaction equation

HRID 1919840 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]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]([CH3:13])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6417Pivalic acidHCID 47383082-Methylpyridine-3-carbonitrile2×HCID 194251856-Tert-butylpyridine-3-carbonitrile

Product 1

HCID 579390166-Tert-butyl-2-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 2-methyl-nicotinonitrile (intermediate 30) (216 mg, 1.7 mmol), pivalic acid (868 mg, 8.5 mmol), AgNO3 (38.5 mg, 0.23 mmol), (NH4)2S2O8 (504 mg, 2.2 mmol) and 3.75 ml 10% H2SO4. Purification by normal phase chromatography with 100% heptane to 90/10 Heptane/EA yielded 240 mg of a mixture of both mono and di-t-butylated pyridines. Material used crude in the preparatin of [1-(6-tert-butyl-2-methylpyridin-3-yl)ethyl]amine (intermediate 32) below.

Workup

  1. customPurification by normal phase chromatography with 100% heptane to 90/10 Heptane/EA

Sources & evidence

ORD record
ord-aa1193b09b964b6b831a5d9567f69d2f
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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