1-Methylpyrrole → (4-Methoxyphenyl)(1-methyl-1H-pyrrol-2-yl)methanone

HRID 841029Notes

Reaction equation

HRID 841029 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)=[O:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73041-MethylpyrroleHCID 7477p-Anisoyl chloride

Product 1

HCID 774541(4-Methoxyphenyl)(1-methyl-1H-pyrrol-2-yl)methanoneYield 28.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5 g (0.06 mole) N-methylpyrrole and 13.3 g (0.078 mole) of 4-methoxybenzoyl chloride in 50 mL of dry toluene was heated under reflux overnight with an argon stream bubbling through the reaction mixture. After cooling, 40 mL of 20% 3-dimethylaminopropylamine in H2O was added and the mixture stirred for 45 minutes. Diethyl ether was added and the organic solution was washed with 1N HCl, NaHCO3, water, brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue recrystallized from ethanol to give 3.68 g of product: mp. 66-68° C.; mass spectrum (CH4—Cl) m/z=216 (M+1); NMR (CDCl3) d 7.85 (d, 2 H); 6.9-7.1 (d,s, 3 H); 6.7 (d, 1 H); 6.15 (d, 1 H); 4.1 (s, 3 H); 3.9 (s, 3 H). Anal Calcd for C13H13NO2: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.59; H, 6.06; N, 6.43.

Workup

  1. temperatureunder reflux overnight with an argon stream
  2. custombubbling through the reaction mixture
  3. temperatureAfter cooling
  4. addition40 mL of 20% 3-dimethylaminopropylamine in H2O was added
  5. additionDiethyl ether was added
  6. washthe organic solution was washed with 1N HCl, NaHCO3, water, brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated in vacuo
  9. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-f875ae59c8f54127825325637b963f48
Source dataset
uspto-grants-2002_04
Patent number
US06369228B2

Reaction notes

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