1-Bromopropane → HCID 14500637, compound

HRID 1761590Notes

Reaction equation

HRID 1761590 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[C:9]([C:11]1[NH:12][CH:13]=[CH:14][CH:15]=1)=[O:10])([O-:5])=[O:4].Br[CH2:20][CH2:21][CH3:22].C(OCC)(=O)C>CN(C)C=O>[CH2:20]([N:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9](=[O:10])[C:8]1[CH:16]=[CH:17][CH:18]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14500627HCID 14500627, compound

Product 1

HCID 14500637HCID 14500637, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

50% Sodium hydride 4 g (160 mmol) in mineral oil was suspended, under nitrogen atmosphere, in 250 ml of anhydrous dimethylformamide. A solution of 15 g (69 mmol) of 2-(3-nitrobenzoyl)pyrrole, prepared, for example, as described in Preparation 3A, in 50 ml of anhydrous dimethylformamide was added thereto, at room temperature, in a dropwise fashion and under stirring. The resulting mixture was stirred for 12 additional hours and then a solution of 18 ml (197 mmol) of 1-bromopropane in 50 ml of dry dimethylformamide was added. The reaction mixture was stirred for 18 hours further and thereafter poured into 1000 ml of ethyl acetate, washed with water (5×500 ml), dried and evaporated in vacuo. Purification of the residue by column chromatography on 500 g of silica gel, using hexane-ethyl acetate (90:10) as eluant provided 17.61 g (98%) of 1-propyl-2-(3'-nitrobenzoyl)pyrrole, the title compound, as an oil.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred for 12 additional hours
  3. stirringThe reaction mixture was stirred for 18 hours further
  4. washwashed with water (5×500 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customPurification of the residue by column chromatography on 500 g of silica gel

Sources & evidence

ORD record
ord-2b66c8569aed48beb70bb3a22d23c74a
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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