Thionyl Chloride → 9,10-Dihydro-9,10-methanoanthracene-9-carbonitrile

HRID 27959Notes

Reaction equation

HRID 27959 reaction equation
[CH:1]1[C:14]2[C:13]3([C:16]([NH2:18])=O)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH:11]1[C:12]2[C:13]3([C:16]#[N:18])[CH2:15][CH:6]([C:5]4[C:14]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20519978HCID 20519978, compound

Product 1

HCID 130690839,10-Dihydro-9,10-methanoanthracene-9-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 9,10-dihydro-9,10-methanoanthracene-9-carboxamide (30 mg) and thionyl chloride (0.15 ml) in toluene (1 ml) was refluxed for 18 hours. Evaporation of toluene and excess thionyl chloride gave 9,10-dihydro-9,10-methanoanthracene-9-carbonitrile. M.P. 120°-123° C.

Workup

  1. customEvaporation of toluene and excess thionyl chloride

Sources & evidence

ORD record
ord-7228baf96751485cac0a2486a5a743b6
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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