Hydrazine → 1-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
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