Acetic Acid → 1-Methyl-3-(2-nitroethenyl)-1H-pyrrole

HRID 1414741Notes

Reaction equation

HRID 1414741 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3]1.[N+:9]([CH3:12])([O-:11])=[O:10].C(N)C1C=CC=CC=1.C(O)(=O)C>C(O)C>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:12][N+:9]([O-:11])=[O:10])=[CH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 7504BenzylamineHCID 37513731-methyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 537829721-Methyl-3-(2-nitroethenyl)-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14.9g (0.137 mole) of 1-methylpyrrole-3-carboxaldehyde, 7.3 ml (0.137 mole) of nitromethane, 2.3 ml (.021 mole) of benzyl amine and 1.2 ml (.021 mole) of acetic acid in 20 ml of absolute ethanol is warmed briefly and stirred for 6 hours. It is then cooled and the precipitated solid is collected, giving as a yellow solid, 1-methyl-3-(2-nitrovinyl)pyrrole; m.p. 90°-92° C.

Workup

  1. temperatureIt is then cooled
  2. customthe precipitated solid is collected

Sources & evidence

ORD record
ord-c806e8ab1b5e4814919563ab7a52c6ea
Source dataset
uspto-grants-1977_01
Patent number
US04002643

Reaction notes

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