Hydrazine hydrate (1:1) → HCID 178439404, compound

HRID 1914857Notes

Reaction equation

HRID 1914857 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[NH2:9][NH2:10].O>C(O)C>[CH:2]([C:3]1[CH:4]=[C:5]([NH2:6])[NH:10][N:9]=1)([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 178439404HCID 178439404, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methyl-3-oxopentanenitrile (Compound [CCLX]) (8.8 g, 79.2 mmol, 1.00 equiv) and NH2NH2.H2O (80%, 7.5 g, 120 mmol, 1.50 equiv) in ethanol (300 mL) was heated to reflux for 1 h under nitrogen. After removed the solvent under vacuum, the residue was loaded onto a silica gel column with dichloromethane/methanol as an eluent to give Compound [CCLXI] as a yellowish oil: LC-MS m/e 126 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 5.17 (s, 1H), 2.75 (septet, J=6.9 Hz, 1H), 1.14 (d, J=6.9 Hz, 6H).

Workup

  1. temperatureto reflux for 1 h under nitrogen
  2. customAfter removed the solvent under vacuum
  3. customto give Compound [CCLXI] as a yellowish oil

Sources & evidence

ORD record
ord-6c029f8b8e5f475e8e7fa69484850cb9
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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