Hydrochloric Acid → HCID 68902066, compound

HRID 1818907Notes

Reaction equation

HRID 1818907 reaction equation
[CH2:1]1[CH2:5]OC[CH2:2]1.CN1C(=O)CCC1.Cl[C:14]1[CH:21]=[C:20]([CH3:22])[C:17]([C:18]#[N:19])=[C:16]([O:23][CH3:24])[N:15]=1.C([Mg]Br)CC.Cl>C(OC(=O)C)C>[CH3:24][O:23][C:16]1[N:15]=[C:14]([CH2:2][CH2:1][CH3:5])[CH:21]=[C:20]([CH3:22])[C:17]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10535454HCID 10535454, compoundHCID 22156051tetrahydrofuran N-methylpyrrolidinoneHCID 178455851HCID 178455851, compound

Product 1

HCID 68902066HCID 68902066, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A transparent red-colored THF/NMP(50 mL/5 mL) solution of 6-chloro-2-methoxy-4-methyl-nicotinonitrile (2.00 g, 11.0 mmol) and Fe (acac)3 (387 mg, 1.1 mmol) was slowly added with 11 mL of n-propylmagnesium bromide (2M solution in diethyl ether) and then stirred for about 20 minutes. The mixture was then added with 10 mL of 1M HCl solution 10 mL and diluted with 300 mL of ethylacetate. The resulting organic layer was washed with water and a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and then filtered. A silica gel column chromatography (10% EtOAc/Hexane) was performed on the residue obtained by concentrating the above filtrate under reduced pressure and obtained 2.23 g (88%) of 2-methoxy4-methyl-6-propyl-nicotinonitrile in colorless oil.

Workup

  1. washThe resulting organic layer was washed with water
  2. dry with materiala saturated solution of sodium chloride, dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. customobtained
  5. concentrationby concentrating the above filtrate under reduced pressure

Sources & evidence

ORD record
ord-a3973e16918049d3bbaebe4795a1b7f8
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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