Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 66644209, compound

HRID 1931074Notes

Reaction equation

HRID 1931074 reaction equation
[ClH:1].Cl.[CH:3]1([CH2:6][NH:7][NH2:8])[CH2:5][CH2:4]1.[CH3:9][C:10]([CH3:17])([CH3:16])[C:11](=O)[CH2:12][C:13]#[N:14]>C(O)C>[ClH:1].[C:10]([C:11]1[CH:12]=[C:13]([NH2:14])[N:7]([CH2:6][CH:3]2[CH2:5][CH2:4]2)[N:8]=1)([CH3:17])([CH3:16])[CH3:9]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 43810474(Cyclopropylmethyl)hydrazine--hydrogen chloride (1/2)

Product 1

HCID 66644209HCID 66644209, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 27B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.69 g, 93 mmol) in ethanol (50 mL) was refluxed at 90° C. for 6 hours. The mixture was concentrated under reduced pressure and ethyl acetate (20mL) added to the residue. The white solid precipitate was filtered, washed with ether and dried to yield 17.5 g (90%) of title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.02 (d, J=7.12 Hz, 2H), 5.53 (s, 1H), 6.91 (s, 2H), 14.05 (s, 1H); H); MS (DCI) m/z 294 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate (20mL)
  2. additionadded to the residue
  3. filtrationThe white solid precipitate was filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-faa7c7aae34f41c591ecad2d8457dae1
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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