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

HRID 536709Notes

Reaction equation

HRID 536709 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 (20 mL) 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); MS (DCI) m/z 294 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-d470002338e24e90b2fc5c230bad2bfc
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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