Hydrazine → 5-Cyano-2-cyclobutyl-4-methylbenzohydrazide

HRID 1487978Notes

Reaction equation

HRID 1487978 reaction equation
[C:1]([C:3]1[C:4]([CH3:17])=[CH:5][C:6]([CH:13]2[CH2:16][CH2:15][CH2:14]2)=[C:7]([CH:12]=1)[C:8](OC)=[O:9])#[N:2].[NH2:18][NH2:19]>CCO>[C:1]([C:3]1[C:4]([CH3:17])=[CH:5][C:6]([CH:13]2[CH2:16][CH2:15][CH2:14]2)=[C:7]([CH:12]=1)[C:8]([NH:18][NH2:19])=[O:9])#[N:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68288958Methyl 5-cyano-2-cyclobutyl-4-methylbenzoate2×

Product 1

HCID 682889185-Cyano-2-cyclobutyl-4-methylbenzohydrazideYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 5-cyano-2-cyclobutyl-4-methylbenzoate (compound 89.4, 2.0 g, 8.73 mmol) in EtOH (10 mL) was added anhydrous hydrazine (2 mL, excess) at room temperature. The mixture was heated at 90° C. overnight, then the mixture was cooled to room temperature and partitioned between water (60 mL) and EtOAc (200 mL). The organic layer was washed with water (×2), brine, dried (Na2SO4), filtered, and concentrated to yield 1.9 g (95%) of the title compound as a white solid. m/z (ES+) 230 (M+H)+. 1H NMR (400 MHz, Chloroform-d) δ 7.52 (s, 1H), 7.32 (s, 1H), 6.91 (br, 1H), 4.08 (br, 2H), 3.89 (m, 1H), 2.61-2.52 (m, 3H), 2.42-2.28 (m, 2H), 2.18-1.98 (m, 3H), 1.91-1.78 (m, 1H).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. custompartitioned between water (60 mL) and EtOAc (200 mL)
  3. washThe organic layer was washed with water (×2), brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-419d90f2a81b4ccdbfe41ac5f73db8de
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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