Dimethylcarbamoyl Chloride → 4-Pentyl-2-cyanopyridine

HRID 1374457Notes

Reaction equation

HRID 1374457 reaction equation
CO[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](O)=O)[CH:4]=1.C[Si](C#N)(C)C.CO[C:20]1[CH:25]=[CH:24][N+]([O-])=[CH:22][CH:21]=1.C[N:28](C)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:22]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:28])[CH:4]=1)[CH2:21][CH2:20][CH2:25][CH3:24]

Participants

7

Reactant 5

HCID 6598Dimethylcarbamoyl ChlorideHCID 707434-Methoxypyridine N-oxideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 20500994-Methoxypyridine-2-carboxylic acid

Product 1

HCID 210760834-Pentyl-2-cyanopyridineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxypyridine-2-carboxylic acid, compound 10(b) (R9=methoxy), was made employing general Method P. To trimethylsilyl cyanide (0.95 g, 9.6 mmol), 4-methoxypyridine N-oxide (1 g, 8 mmol) in DCM (10 mL) was added, followed by dimethylcarbamoyl chloride (1.03 g, 9.6 mmol) in DCM (10 mL), dropwise. After stirring at room temperature overnight, sodium bicarbonate (100 mL, 10%) was added, and the organic layer was separated. The aqueous layer was extracted twice by DCM (50 mL each). The combined organic layer was dried over magnesium sulfate and the solvent was removed to obtain product, compound 10a (0.97 g, 90%):

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice by DCM (50 mL each)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-866b16b1d87f4cac9b78793066c6c010
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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