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

HRID 1271454Notes

Reaction equation

HRID 1271454 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-df870f3ccb4549ee8dc04649fd6b9513
Source dataset
uspto-grants-2007_04
Patent number
US07205331B2

Reaction notes

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