Hydrazine hydrate (1:1) → HCID 178424217, compound

HRID 510415Notes

Reaction equation

HRID 510415 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][CH:5]([C:8](=O)[CH3:9])[C:6]#[N:7].O.[NH2:16][NH2:17]>C(O)C>[CH3:9][C:8]1[C:5]([CH2:4][C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[CH3:1])=[C:6]([NH2:7])[NH:17][N:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867248862-(2-Methylbenzyl)-3-oxobutanenitrile

Product 1

HCID 178424217HCID 178424217, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2-methylbenzyl)-3-oxobutanenitrile (7.39 g, 39.5 mmol) in ethanol (400 mL) was added hydrazine hydrate (1.97 g, 39.5 mmol) and stirred under reflux for 16 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel column (petroleum ether/ethyl acetate=1/1 then DCM:methanol=40:1) to provide the titled compound (3.005 g, 38%) as a yellow solid; LC/MS: MS (ES+) m/e 202 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 2.12 (s, 3H), 2.33 (s, 3H), 3.63 (s, 2H), 7.07-7.17 (m, 4H).

Workup

  1. temperatureunder reflux for 16 h
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column (petroleum ether/ethyl acetate=1/1

Sources & evidence

ORD record
ord-518e79a1ec9140d0ac67ff96af27ceec
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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