2-Acetylpyrrole → HCID 18519882, compound

HRID 1368061Notes

Reaction equation

HRID 1368061 reaction equation
[C:1]([C:4]1[NH:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19](Cl)=[O:20].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19]([C:7]1[CH:8]=[C:4]([C:1](=[O:3])[CH3:2])[NH:5][CH:6]=1)=[O:20]

Participants

5

Reactant 3

HCID 140792-AcetylpyrroleHCID 752462-Naphthoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18519882HCID 18519882, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 7.5 g (0.069 mole) of 2-acetylpyrrole, 17 g (0.089 mole) of 2-naphthalenoyl chloride and 18.3 (0.14 mole) of aluminum chloride in 200 mL of 1,2-dichloroethane was stirred for 4 h and then heated at 65° C. for 1.5 h. After cooling, the reaction mixture was poured into 2N HCl/ice. The organics were separated, washed with water, NaHCO3, water, brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue recrystallized from EtOAc to give 9.25 g (51%) of 1-[4-(2-naphthalenoyl)-1H-pyrrol-2-yl]ethanone. mp 172-174° C. CIMS m/z 264 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.4 (Ar, 1H); 8.0-7.9 (Ar, 4H); 7.7-7.55 (Ar, 3H); 7.5 (Ar, 1H); 2.55 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customThe organics were separated
  3. washwashed with water, NaHCO3, water, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe residue recrystallized from EtOAc

Sources & evidence

ORD record
ord-aa51254bb24e4a9a9e6ac16bd7c3fc11
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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