Formaldehyde → 2,3,4,5-Tetramethylpyrrole

HRID 1834423Notes

Reaction equation

HRID 1834423 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:13](OCC)=O)=[C:5]([CH3:12])[C:6]=1[C:7](OCC)=O.I.C=O>C(O)(=O)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:13])=[C:5]([CH3:12])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24841Hydrogen iodideHCID 75526Diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate

Product 1

HCID 704842,3,4,5-Tetramethylpyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,4-Dimethyl-3,5-dicarbethoxy-pyrrole (2.4 g), acetic acid (35 ml), aq. hydriodic acid (35 ml) and paraformaldehyde (1.2 g) were heated at 100° C. for 4 hours under a stream of nitrogen. The crude product was obtained as in Example 5 then distilled (15 mm, 65° C.) to yield 0.44 g (36%), m.p. 107°-109°.

Sources & evidence

ORD record
ord-0baf3f5bc1ad4bf69c54939ae6114f89
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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