Hydrazine hydrate (1:1) → HCID 178509121, compound

HRID 510427Notes

Reaction equation

HRID 510427 reaction equation
[Cl:1][C:2]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][CH:5]([C:8](=O)[C:9]([F:12])([F:11])[F:10])[C:6]#[N:7].O.[NH2:20][NH2:21]>C(O)C>[Cl:1][C:2]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:8]([C:9]([F:10])([F:11])[F:12])=[N:20][NH:21][C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 71270874HCID 71270874, compound

Product 1

HCID 178509121HCID 178509121, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,3-dichlorobenzyl)-4,4,4-trifluoro-3-oxobutanenitrile (10.0 g, 33.77 mmol) in ethanol (800 mL) was added hydrazine hydrate (1.86 g, 37.15 mmol) and the resulting solution was 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=2/1) and reverse-phase Prep-HPLC to provide the titled compound (1.6 g, 15%) as a yellow oil; LC/MS: MS (ES+) m/e 310 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.85 (s, 2H), 6.78 (dd, J=1.2, 7.8 Hz, 1H), 7.25 (t, J=7.8 Hz, 1H), 7.47 (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=2/1) and reverse-phase Prep-HPLC

Sources & evidence

ORD record
ord-ec2bf31a438a4a25a69566b79f7f754e
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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