4-Methylpyridine → HCID 86742908, compound

HRID 620001Notes

Reaction equation

HRID 620001 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[CH2:8]([Br:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[CH2:8]([Br:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[NH+:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 79634-MethylpyridineHCID 813551-Bromodocosane

Product 1

HCID 86742908HCID 86742908, compound

Procedure

Referring to FIG. 1, γ-picoline (VI) has quaternised with docosyl bromide (n-C22H45Br) at 125° C. to produce γ-picolinium docosyl bromide (VII). This compound was then condensed with N,N-dimethyl-p-amino-benzaldehyde in refluxing methanol in the presence of piperidine for 16 hours. This reaction produced the intermediate alcohol IX presumably via an intermediate VIII. The intermediate alcohol IX eliminated water to give the stilbazolium dye X, which crystallised out on cooling the reaction mixture. Dye X was filtered off and purified by repeated recrystalisation from methanol (yield 47%).

Sources & evidence

ORD record
ord-f97d15606caa4b0fabca6d2b7d683d10
Source dataset
uspto-grants-1989_04
Patent number
US04818616

Reaction notes

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