Acrylonitrile → HCID 15505591, compound

HRID 1747439Notes

Reaction equation

HRID 1747439 reaction equation
[Cl-].[C:2]([CH2:5][N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])(O)=O.[C:13](#[N:16])[CH:14]=C.CCN(CC)CC>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:12][C:7]1[N:6]2[C:11]([CH:10]=[CH:9][CH:8]=1)=[C:14]([C:13]#[N:16])[CH:2]=[CH:5]2

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 30839496266-22-4

Product 1

HCID 15505591HCID 15505591, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of crude 1-Carboxymethyl-2-methyl-pyridinium chloride (7 g, 0.037 mol) in toluene (50 mL) were added acrylonitrile (7.4 mL, 0.11 mol), MnO2 (6.5 g, 0.075 mol) and Et3N (2 mL) at room temperature under nitrogen atmosphere. The solution was heated to 90 C and was stirred at the same temperature for 12 hours. The solution was cooled down and was filtered to remove the excess MnO2. The filtrate was concentrated and the residue was purified by CombiFlash with 10% EtOAc in Hexane to afford the desirable product 5-Methyl-indolizine-1-carbonitrile, CAS: 5-Methyl-indolizine-1-carbonitrile (3 g, 52%) as a white solid.

Workup

  1. temperatureThe solution was heated to 90 C
  2. temperatureThe solution was cooled down
  3. filtrationwas filtered
  4. customto remove the excess MnO2
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by CombiFlash with 10% EtOAc in Hexane

Sources & evidence

ORD record
ord-06dc95c1c4f845009c6b232b77c86aea
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…