Pivalic acid → 6-Tert-butyl-2-chloropyridine-3-carbonitrile

HRID 1919831Notes

Reaction equation

HRID 1919831 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].[Cl:13]C1N=CC=CC=1C#N.C(O)(=O)C(C)(C)C>[N+]([O-])([O-])=O.[Ag+].OS(O)(=O)=O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([Cl:13])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6417Pivalic acidHCID 810792-ChloronicotinonitrileHCID 194251856-Tert-butylpyridine-3-carbonitrile

Product 1

HCID 532788766-Tert-butyl-2-chloropyridine-3-carbonitrileYield 42%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 1118Sulfuric AcidSolvent

Procedure

The title compound was synthesized according to the procedure described for the synthesis of 6-tert-butylnicotinonitrile starting from 2-chloronicotinonitrile (3.91 g, 28 mmol), pivalic acid (14.4 g, 141 mmol), AgNO3 (0.622 g, 3.66 mmol), (NH4)2S2O8 (8.36 g, 36.6 mmol) and 50 ml 10% H2SO4. Purified by normal phase chromatography using 100 heptane to 95/5 heptane/ethyl acetate. (Yield: 42%, 2.3 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (s, 9 H), 7.36 (d, J=8.20 Hz, 1 H), 7.88 (d, J=8.20 Hz, 1 H).

Workup

  1. customPurified by normal phase chromatography

Sources & evidence

ORD record
ord-407fbd4cb608430bb986a514e4029a9b
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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