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

HRID 1069149Notes

Reaction equation

HRID 1069149 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. Step D: Preparation of 2-cyano-3,4,4-trimethylpentanoic acid

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-00dfc117e26848d8b4ccfc89ef271880
Source dataset
uspto-grants-2001_06
Patent number
US06251947B1

Reaction notes

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