Dimethylformamide → 4-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 24333Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[CH:9][NH:8][C:7]=1[CH3:17])=[O:5])[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:26]=[O:27])C>>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[C:9]([CH:26]=[O:27])[NH:8][C:7]=1[CH3:17])=[O:5])[CH3:2]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 54559518HCID 54559518, compound

Product 1

HCID 542399104-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 96%

Procedure

4-(3-Dimethylaminopropyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (600 mg, 2.5 mmol) was formylated using POCl3 and DMF to give 645 mg (96%) of 4-(3-dimethylamino-propyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester.

Sources & evidence

ORD record: ord-da097ef5a2bc4a56a8b1a1523f235358
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855730B2

Reaction notes

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