Ketone, 2,4-dimethylpyrrol-3-yl methyl → HCID 20373142, compound

HRID 1834433Notes

Reaction equation

HRID 1834433 reaction equation
CO[CH:3](OC)[CH2:4][NH2:5].[CH3:8][C:9]1[NH:10][CH:11]=[C:12]([CH3:17])[C:13]=1[C:14](=[O:16])[CH3:15]>I.[PH2](O)=O>[CH3:8][C:9]1[NH:10][C:11]([CH2:3][CH2:4][NH2:5])=[C:12]([CH3:17])[C:13]=1[C:14](=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 20373142HCID 20373142, compound

Reagents, catalysts & solvents 2

HCID 24841Hydrogen iodideSolventHCID 4124402Phosphinic AcidSolvent

Procedure

Aminoacetaldehyde dimethyl acetal (0.75 ml) was added to a stirred solution of 2,4-dimethyl-3-acetyl-pyrrole (0.548 g) in 10 ml of hydriodic acid and 2 ml of hypophosphorous acid. The solution was stirred for 4 hr. at 35° then evaporated in a shallow dish in a vacuum disiccator, finally at 0.1 mm, and the residue twice slurried and filtered with acetone. The clarified solution of the solid in water (5 ml) was made strongly alkaline with KOH, saturated with potassium carbonate, and extracted repeatedly with ether. The ether solution (125 ml) was concentrated, adding n-pentane toward the end, to precipitate the product (29%) as pale yellow prisms, m.p. 106.5°-107.5°. Anal. Calc. for C10H16N2O: C, 66.63; H, 8.95; N, 15.54; neut. equiv. 180. Found: C, 66.51; H, 8.89; N, 15.62; neut. equiv. 182.

Workup

  1. customat 35° then evaporated in a shallow dish in a vacuum disiccator, finally at 0.1 mm
  2. filtrationfiltered with acetone
  3. extractionextracted repeatedly with ether
  4. concentrationThe ether solution (125 ml) was concentrated
  5. additionadding n-pentane toward the end
  6. customto precipitate the product (29%) as pale yellow prisms, m.p. 106.5°-107.5°

Sources & evidence

ORD record
ord-407956244c03428095b65ef8e13585f0
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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