Hydrazine → 1-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile

HRID 720775Notes

Reaction equation

HRID 720775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23]#[N:24])[N:5]([CH2:8][CH2:9][CH:10]([N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:11])[C:6]=1[CH3:7].NN>C(O)C>[NH2:12][CH:10]([CH3:11])[CH2:9][CH2:8][N:5]1[C:6]([CH3:7])=[C:2]([Cl:1])[CH:3]=[C:4]1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 21895242HCID 21895242, compound

Product 1

HCID 218952681-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.2 g (9.4 mmol) of 4-chloro-1-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]-5-methyl-1H-pyrrole-2-carbonitrile and 4.8 mL (94 mmol) of hydrazine in ethanol was heated at reflux for 60 min and cooled to room temperature. Precipitated solids were filtered and rinsed with ethyl acetate and the filtrate was concentrated to afford 1-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile as an oil.

Workup

  1. temperatureat reflux for 60 min
  2. customPrecipitated solids
  3. filtrationwere filtered
  4. washrinsed with ethyl acetate
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e48fbf431f624e6db31ec62414253cf5
Source dataset
uspto-grants-2006_11
Patent number
US07135585B2

Reaction notes

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