Ammonia → HCID 21411778, compound

HRID 2071651Notes

Reaction equation

HRID 2071651 reaction equation
N.[K].[N:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.Cl[CH2:11][CH2:12][O:13][CH:14]=[CH2:15].[Cl-].[NH4+]>C(OCC)C>[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:15][CH2:14][O:13][CH:12]=[CH2:11])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 79634-MethylpyridineHCID 80742-Chloroethyl vinyl etherHCID 25517Ammonium ChlorideHCID 5462222Potassium

Product 1

HCID 21411778HCID 21411778, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by potassium metal (20 gms) in 1 gram pieces over a period of 20 minutes. To the resulting solution gamma-picoline (46.6 gms) was added over a period of 3 minutes and a deep yellow colour was allowed to develop over a period of 2 hours. Vinyl chloroethyl ether (53 gms) was added as quickly as the exothermic reaction allowed and the mixture was stirred for a further 2 hours. Solid ammonium chloride (25 gms) was then added in small portions, followed by diethyl ether (1 liter). The ammonia was allowed to evaporate overnight and the residual mixture was filtered. The solvent was evaporated from the filtrate and the residual oil was distilled to yield vinyl 3-(4-pyridyl)-prop-1-yl ether (61 gms, 75% conversion); b.p. 90°-96° C/1 mm Hg.

Workup

  1. customquickly as the exothermic reaction
  2. customto evaporate overnight
  3. filtrationthe residual mixture was filtered
  4. customThe solvent was evaporated from the filtrate
  5. distillationthe residual oil was distilled

Sources & evidence

ORD record
ord-a919e8aa37684855abdf321ae3da9626
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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