Malononitrile → [3,4'-BIPYRIDINE]-5-CARBONITRILE,6-METHOXY-

HRID 1463052Notes

Reaction equation

HRID 1463052 reaction equation
C[N:2]([CH3:13])[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH:5]=O.[C:14](#[N:18])[CH2:15]C#N.[CH3:19][O-:20].[Na+]>CO>[C:14]([C:15]1[C:13]([O:20][CH3:19])=[N:2][CH:3]=[C:4]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[CH:5]=1)#[N:18]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 10942334Sodium MethoxideHCID 541977173-Dimethylamino-2-(4-pyridinyl)acrolein

Product 1

HCID 13345674[3,4'-BIPYRIDINE]-5-CARBONITRILE,6-METHOXY-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nantka-Namirski et al. [Pol. J. Pharmacol. Pharm. 30, No. 5, pp. 707-712 (1978)] in a paper entitled "Cancerostatics III. Synthesis and Some Chemical Transformations of 3-cyano-5-(pyridyl-4-)pyrid-2-one" show, inter alia, the reaction of 3-dimethylamino-2-(4-pyridinyl)acrolein with malononitrile and sodium methoxide in methanol at room temperature to produce 3-cyano-2-methoxy-5-(4-pyridinyl)pyridine. Also shown in this paper is 2-chloro-3-cyano-5-(4-pyridinyl)pyridine, disclosed in the instant application as an intermediate to prepare 3-cyano-2-methoxy-5-(4-pyridinyl)pyridine.

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-91a2d2dd8b344ed4892033df27e54a32
Source dataset
uspto-grants-1984_07
Patent number
US04463008

Reaction notes

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