(1-Methylpyrrol-2-yl)-(3-nitrophenyl)methanone → 3-(1-Methylpyrrol-2-ylmethyl)nitrobenzene

HRID 365613Notes

Reaction equation

HRID 365613 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)=O)([O-:3])=[O:2].C([BH3-])#N.[Na+]>[I-].[Zn+2].[I-].ClCCCl>[CH3:14][N:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH2:7][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 2308530(1-Methylpyrrol-2-yl)-(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 232857013-(1-Methylpyrrol-2-ylmethyl)nitrobenzeneYield 75.7%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-(3-nitrobenzoyl)-1-methylpyrrole (5.0 g, 21.7 mmol) [prepared as in Example 8, Step (a)], zinc iodide (10.38 g, 32.5 mmol), sodium cyanoborohydride (10.22 g, 162.7 mmol), and 1,2-dichloroethane (300 ml) was refluxed for 16 h. The reaction mixture was cooled to room temperature, filtered through Celite®, and then concentrated to dryness. Purification of the residue on a Florisil® column (hexane-acetone, 98:1) gave 3-(1-methylpyrrol-2-ylmethyl) nitrobenzene (3.55 g, 75%) as a solid. ##STR43##

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationfiltered through Celite®
  3. concentrationconcentrated to dryness
  4. customPurification of the residue on a Florisil® column (hexane-acetone, 98:1)

Sources & evidence

ORD record
ord-f8d43bc492d24d809c3178ee443d5b4a
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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