Pyridine → HCID 13281344, compound

Reaction equation

Cl[C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N:18]1C=CC=C[CH:19]=1>>[CH:5]1[C:6]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:2]([C:19]#[N:18])=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 1049Pyridine

HCID 13281343HCID 13281343, compound

Product 1

HCID 13281344HCID 13281344, compound

Procedure

The reaction of 4-chloro-5,6,7,8-tetrahydrodibenzo[a,c]cyclooctene (3.3 g, 0.014 mole), cuprous cyanide (2.44 g, 0.027 mole) and pyridine (2.5 g, 0.027 mole) produced 5,6,7,8-tetrahydrodibenzo[a,c]cycloocten-4-carbonitrile as an oil (60% product, 40% starting material by gas chromatography). The IR spectrum possessed an adsorption at 4.45μ indicating a CN group.

Sources & evidence

ORD record: ord-05824495702e4cd0b95b9d54b41176c1
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04451484

Reaction notes

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