Pyrrole-2-carboxaldehyde → 1-[(4,5-Dimethoxy-2-nitrophenyl)methyl]-1H-pyrrole-2-carboxaldehyde

HRID 2184449Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9].[CH3:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH2:16]Br)=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH2:16][N:3]2[CH:7]=[CH:6][CH:5]=[C:4]2[CH:8]=[O:9])=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (0.724 g, 60% suspension in oil) in N,N-dimethylformamide (50 mL) was added pyrrole 2-carboxaldehyde (1.7 g, 18.1 mmol) and the reaction mixture was stirred for 30 minutes. It was then cooled to 0° C. and 4,5-dimethoxy-2-nitrobenzyl bromide (5.0 g, 1 equiv) was added dropwise over 20 minutes. After the addition, the reaction mixture was stirred at room temperature for 3 hours. It was then diluted with ethyl acetate (450 mL), washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude product was triturated with water, filtered and washed with water. This material was dried over anhydrous potassium carbonate in vacuo to provide the title compound as a yellow crystalline solid (4.97 g), m.p. 109-112° C., which was used as such in the next step.

Workup

additionAfter the addition
stirringthe reaction mixture was stirred at room temperature for 3 hours
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated to dryness
customThe crude product was triturated with water
filtrationfiltered
washwashed with water
dry with materialThis material was dried over anhydrous potassium carbonate in vacuo

Sources & evidence

ORD record: ord-41d5697da93844aaa9123f1992552625
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900200B2

Reaction notes

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