Hydrazine hydrate (1:1) → HCID 178441179, compound

HRID 1914851Notes

Reaction equation

HRID 1914851 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[NH2:10][NH2:11].O>CCO>[C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[NH:11][N:10]=1)([CH3:9])([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 178441179HCID 178441179, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4-dimethyl-3-oxopentanenitrile (Compound [CCLII]) (7 g, 55.9 mmol, 1.00 equiv) and NH2NH2.H2O (4.5 g, 140 mmol, 2.00 equiv) in EtOH (100 mL) was stirred for 7 h at 110° C. under nitrogen. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). After cooling, the resulting solution was concentrated under vacuum and diluted with 50 mL of water. The resulting solution was extracted with CH2Cl2, dried and concentrated under reduced pressure. The residue was loaded onto a silica gel column with ethyl acetate/petroleum ether as the eluent to Compound [CCXXXIV] as a yellowish oil: LCMS (m/e) 140 (M+H); 1H NMR (300 MHz, DMSO-d6) δ ppm 5.18 (s, 1H), 1.19 (s, 9H). Amount obtained: 7.6 g, 97% yield.

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting solution was concentrated under vacuum
  3. additiondiluted with 50 mL of water
  4. extractionThe resulting solution was extracted with CH2Cl2
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customAmount obtained

Sources & evidence

ORD record
ord-4588b4a2319b4e2c94e7f6b5cd722d64
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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