Hydrazine hydrate (1:1) → HCID 178434675, compound

HRID 510418Notes

Reaction equation

HRID 510418 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][CH:5]([C:8](=O)[CH3:9])[C:6]#[N:7].O.[NH2:17][NH2:18]>C(O)C>[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:5]1[C:8]([CH3:9])=[N:17][NH:18][C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 712707302-(2,3-Dichlorobenzyl)-3-oxobutanenitrile

Product 1

HCID 178434675HCID 178434675, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,3-dichlorobenzyl)-3-oxobutanenitrile (2.19, 9.05 mmol) in ethanol (400 mL) was added hydrazine hydrate (0.452 g, 9.05 mmol) and the resulting solution was stirred under reflux for 16 h. Then 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 (1.21 g, 52%) as a yellow solid; LC/MS: MS (ES+) m/e 256 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 2.13 (s, 3H), 3.77 (s, 2H), 6.97 (dd, J=1.2, 7.8 Hz, 1H), 7.10 (t, J=7.8 Hz, 1H), 7.33 (dd, J=1.2, 7.8 Hz, 1H)

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-25b83529c8344862afd6abbfd9cd1762
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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