Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 63278673, compound

HRID 1931077Notes

Reaction equation

HRID 1931077 reaction equation
Cl.Cl.[F:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][NH:9][NH2:10])=[CH:6][CH:5]=1.[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:9]([CH2:8][C:7]2[CH:11]=[CH:12][C:4]([F:3])=[CH:5][CH:6]=2)[N:10]=1)([CH3:21])([CH3:20])[CH3:13]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 45074965[(4-Fluorophenyl)methyl]hydrazine--hydrogen chloride (1/2)

Product 1

HCID 63278673HCID 63278673, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (4-fluorobenzyl)hydrazine dihydrochloride (1.0 g, 4.7 mmol, Matrix) in ethyl alcohol (2 mL) was added 4,4-dimethyl-3-oxopentanenitrile (0.6 g, 4.7 mmol, Aldrich). After stirring at 85° C. for 2 h, the reaction mixture was cooled, concentrated, diluted with ethyl acetate (10 mL) and washed with saturated NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain 1.3 g (99%) of the title compound. MS (ESI m/z 248 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate (10 mL)
  4. washwashed with saturated NaHCO3 (10 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e436995ce5548f4bf256e456eda7b59
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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