Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 117729082, compound

HRID 2200057Notes

Reaction equation

HRID 2200057 reaction equation
C(O)(=O)C(O)=O.[CH3:7][O:8][CH2:9][CH2:10][NH:11][NH2:12].[CH3:13][C:14]([CH3:21])([CH3:20])[C:15](=O)[CH2:16][C:17]#[N:18]>C(O)C>[C:14]([C:15]1[CH:16]=[C:17]([NH2:18])[N:11]([CH2:10][CH2:9][O:8][CH3:7])[N:12]=1)([CH3:21])([CH3:20])[CH3:13]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 54593797HCID 54593797, compound

Product 1

HCID 117729082HCID 117729082, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A stirred suspension of (2-methoxyethyl) hydrazine oxalic acid (0.50 g, 2.77 mmol) and 4,4-dimethyl-3-oxopentanenitrile (0.347 g, 2.77 mmol) in ethanol (6 mL) was heated at 85° C. for 4.5 h during which time all solids dissolved. The reaction mixture was allowed to cool overnight and then the solvent was evaporated. The residue was dissolved in dichloromethane (20 mL) and washed with saturated aqueous NaHCO3 (10 mL). The organic layer was separated using a phase separator cartridge and evaporated. The residual oil was dissolved in diethyl ether and evaporated to afford the title compound (0.538 g, 98%) as a solid. 1H NMR (300 MHz, CDCl3): 1.26 (9H, s), 3.33 (3H, s), 3.67 (2H, t, J 4.3 Hz), 3.95 (2H, br s), 4.13 (2H, t, J 4.6 Hz), 5.36 (1H, s).

Workup

  1. dissolutiondissolved
  2. temperatureto cool overnight
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  5. washwashed with saturated aqueous NaHCO3 (10 mL)
  6. customThe organic layer was separated
  7. customevaporated
  8. dissolutionThe residual oil was dissolved in diethyl ether
  9. customevaporated

Sources & evidence

ORD record
ord-53723b496fbb42e98542741206d65df0
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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