Dimethylcarbamoyl Chloride → tert-Butyl 6-cyanopicolinate

HRID 499335Notes

Reaction equation

HRID 499335 reaction equation
[N+:1]1([O-])[C:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C[Si]([C:19]#[N:20])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:19]([C:6]1[N:1]=[C:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:3]=[CH:4][CH:5]=1)#[N:20]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 68456092tert-Butyl 2-pyridinecarboxylate N-oxide

Product 1

HCID 22939377tert-Butyl 6-cyanopicolinateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

A mixture of tert-butyl 2-pyridinecarboxylate N-oxide (12.4 g, 63 mmol), trimethylsilyl cyanide (9.6 g, 96 mmol), N,N-dimethylcarbamoyl chloride (10.3 g, 95 mmol) and nitroethane (80 ml) was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (3; 1, v/v) and recrystallized from tetrahydrofuran-hexane to give the titled compound (11.1 g, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washeluted with hexane-ethyl acetate (3
  3. custom1, v/v) and recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-5a20868b32d7445b802bae29d0cb9228
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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