2,5-Hexanedione → 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzaldehyde

HRID 2371963Notes

Reaction equation

HRID 2371963 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[CH:16][C:11]([CH:12]=CCN)=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.NC1C=CC(C=[O:24])=CC=1.C(CC(=O)C)C(C)=O>>[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[CH:16][C:11]([CH:12]=[O:24])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 80352,5-HexanedioneHCID 111584-AminobenzaldehydeHCID 86745551HCID 86745551, compound

Product 1

HCID 27645504-(2,5-Dimethyl-1H-pyrrol-1-yl)benzaldehyde

Procedure

Similarly prepared is N-acetyl-N-acetyloxy-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-cinnamylamine. The starting material is prepared by first condensing p-amino-benzaldehyde with acetonylacetone to obtain 4-(2,5-di-methyl-1H-pyrrol-1-yl)-benzaldehyde which is in turn condensed with diethyl phosphonoacetaldehyde diethylacetal to obtain 4-(2,5-dimethyl-1H-pyrrol-1-yl)-cinnamaldehyde. The aldehyde is then converted to the oxime and reduced to the hydroxylamine according to previously described procedures.

Workup

  1. customSimilarly prepared

Sources & evidence

ORD record
ord-d3a8c64b060b446c8f7641059b17090b
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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