Dimethylformamide → Pyrrole-2-carboxaldehyde

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.P(Cl)(Cl)(Cl)=[O:14].[CH3:18]N(C)C=O>>[CH3:1][N:2]1[C:6]([CH3:18])=[CH:5][CH:4]=[C:3]1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[NH:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=[O:14]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 10249Nicotyrine

HCID 24813Phosphorus oxychloride

Product 2

HCID 13854Pyrrole-2-carboxaldehyde

HCID 536472703-(1,5-Dimethyl-1H-pyrrol-2-yl)pyridine

Procedure

The 1,5-dimethyl-2-(3-pyridyl) pyrrole is prepared from 1-methyl-2-(3-pyridyl) pyrrole by treatment with phosphorus oxychloride and dimethyl formamide to form a pyrrole-carboxaldehyde which is then subjected to a Wolff-Kishner reduction.

Sources & evidence

ORD record: ord-1d01cb8088724a0e8ba8b62017a91214
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04065561

Reaction notes

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