1-Methylpyrrole → HCID 18519867, compound

HRID 1368058Notes

Reaction equation

HRID 1368058 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:18]

Participants

4

Reactant 2

HCID 73041-MethylpyrroleHCID 752462-Naphthoyl chloride

Product 1

HCID 18519867HCID 18519867, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Methylpyrrole (19.5 g, 0.24 mole) and 2-napthalenoyl chloride (50.0 g, 0.26 mole) 300 mL of dry toluene were heated under reflux overnight with a nitrogen stream bubbling through the reaction mixture. Another 10 mL of N-methylpyrrole was added to the reaction mixture and the reflux was continued for another 38 hr. 100 mL of 20% aqueous 3-(dimethylamino)propylamine was added and stirred for 30 minutes. Et2O/THF was added and the organics were separated off, washed with 1 N HCl, NaHCO3, water, brine and dried (MgSO4). The solvent was evaporated in vacuo to give 51 g (90%) of (2-naphthalenyl)(1-methyl-1H-pyrrol-2-yl)-methanone. mp 108-110° C. CIMS m/z236 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.35 (Ar, 1H); 8.0-7.9 (Ar, 4H); 7.6-7.5 (Ar, 2H); 6.95 (Ar, 1H); 6.8 (Ar, 1H); 6.2 (Ar, 1H); 4.1 (s, 3H).

Workup

  1. temperatureunder reflux overnight with a nitrogen stream
  2. custombubbling through the reaction mixture
  3. additionAnother 10 mL of N-methylpyrrole was added to the reaction mixture
  4. addition100 mL of 20% aqueous 3-(dimethylamino)propylamine was added
  5. additionEt2O/THF was added
  6. customthe organics were separated off
  7. washwashed with 1 N HCl, NaHCO3, water, brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6af1ec6764bf4e05b1741ca9106fbe20
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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