Methanol → 2-Methoxy-3-cyano-5-methylpyrrole

HRID 650267Notes

Reaction equation

HRID 650267 reaction equation
[C:1]([CH:3]([CH2:6][C:7](=O)[CH3:8])[C:4]#[N:5])#[N:2].Cl.CNC.[CH3:14][OH:15]>>[CH3:14][O:15][C:1]1[NH:2][C:7]([CH3:8])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 10473Dimethylamine, hydrochlorideHCID 141917182-(2-Oxopropyl)propanedinitrile

Product 1

HCID 217147462-Methoxy-3-cyano-5-methylpyrrole

Procedure

A solution of 2-cyano-4-oxopentanenitrile (2.75 g) and dimethylamine hydrochloride (16.25 g) in 100 ml of methanol was heated at reflux for 24 h. The mixture was cooled to room temperature and the solvents were removed under reduced pressure. The residue was dissolved in 50 ml of H2O and extracted with EtOAc. The organic extracts were dried over Na2SO4. Silica gel chromatography afforded a white solid (0.8 g), m.p. 105° C.

Workup

  1. temperatureat reflux for 24 h
  2. customthe solvents were removed under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried over Na2SO4

Sources & evidence

ORD record
ord-940d77ae62ca4ffaad97ed4088a27009
Source dataset
uspto-grants-2001_08
Patent number
US06271392B1

Reaction notes

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