Hydrazine hydrate (1:1) → HCID 178490032, compound

HRID 2390785Notes

Reaction equation

HRID 2390785 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([O:18][CH3:19])[CH:12]=2)=O)=[CH:4][N:3]=1.COC(OC)[N:23]([CH3:25])C.O.[NH2:29]N>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([O:18][CH3:19])[CH:12]=3)=[N:29][NH:23][CH:25]=2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 508989412-(2-Chloropyridin-5-yl)-1-(3-methoxy-5-methylphenyl)ethanone

Product 1

HCID 178490032HCID 178490032, compoundYield 62%

Procedure

The keto-enol compound (7.28 g, 26.5 mmol) prepared in Example 63 was refluxed for 12 hours with N,N-dimethylformamide dimethylacetal (24 mL, 204 mmol). Excess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation, and the reaction mixture was dissolved in anhydrous ethanol (150 mL). To this solution was dropwise added hydrazine hydrate (2.65 g, 53 mmol), and stirred at room temperature for 4 hours. The solvent was removed by vacuum distillation. The concentrate was purified through column chromatography (silica gel, ethyl acetate-hexane, 1:2, v/v) to afford the title compound as a red liquid (4.92 g, 62%).

Workup

  1. customExcess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation
  2. dissolutionthe reaction mixture was dissolved in anhydrous ethanol (150 mL)
  3. customThe solvent was removed by vacuum distillation
  4. customThe concentrate was purified through column chromatography (silica gel, ethyl acetate-hexane, 1:2

Sources & evidence

ORD record
ord-d0c025a750ea4ae8a3246436b50a287a
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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