Ammonia → 2,3,4,5-Tetramethylpyrrole

HRID 1834434Notes

Reaction equation

HRID 1834434 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:8](OCC)=O)=[CH:5][C:6]=1[CH3:7].[CH2:13]=O.O.N>C(O)(=O)C.I.[PH2](O)=O>[CH3:8][C:4]1[NH:3][C:2]([CH3:1])=[C:6]([CH3:7])[C:5]=1[CH3:13]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 962WaterHCID 137478Ethyl 4,5-dimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 704842,3,4,5-TetramethylpyrroleYield 53%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 24841Hydrogen iodideSolventHCID 4124402Phosphinic AcidSolvent

Procedure

A solution of 2,3-dimethyl-5-carbethoxy-pyrrole (0.82 g) in acetic acid (10 ml), hydriodic acid (10 ml), hypophosphorous acid (2 ml) and paraformaldehyde (0.6 g) was stirred and heated at 100° under nitrogen for 3 hr. then poured into water. The mixture was made alkaline with ammonia and extracted with ether. The ether was evaporated and the residue distilled (65°, 15 mm) to give the product (53%) m.p. 105°-107°.

Workup

  1. temperatureheated at 100° under nitrogen for 3 hr
  2. extractionextracted with ether
  3. customThe ether was evaporated
  4. distillationthe residue distilled (65°, 15 mm)

Sources & evidence

ORD record
ord-dd93da7e3dfb40c08e1b7917cb26e011
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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