2-Chloro-6-hydrazinopyridine → 3-Phenylprop-2-enenitrile

HRID 1731672Notes

Reaction equation

HRID 1731672 reaction equation
[Na].Cl[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH:9]N)N=1>C(O)C>[C:5](#[N:9])[CH:6]=[CH:7][C:8]1[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3200042-Chloro-6-hydrazinopyridineHCID 5360545Sodium

Product 1

HCID 746673-Phenylprop-2-enenitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As for Example 2, a mixture of 0.23 g. of sodium metal, 50 ml. of absolute ethanol, 7.11 g. of 2-chloro-6-hydrazinopyridine and 6.5 g. of cinnamonitrile yields 7.35 g. of crude product. The crude material is dissolved in dichloromethane, filtered through hydrous magnesium silicate and concentrated while adding hexane to give 5.90 g. of the desired product as off-white crystals, m.p. 187.5°-188.5° C.

Workup

  1. additionAs for Example 2, a mixture of 0.23 g

Sources & evidence

ORD record
ord-7c1f4ac16cc84d8a9ce162953934cf88
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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