1,1-Dimethylhydrazine → HCID 57726009, compound

HRID 1922280Notes

Reaction equation

HRID 1922280 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](Cl)=[O:10])[CH:4]=1.[CH3:12][N:13]([CH3:15])[NH2:14].C(N(CC)C(C)C)(C)C>C1COCC1.O.CCOC(C)=O>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:14][N:13]([CH3:15])[CH3:12])=[O:10])[CH:4]=1

Participants

7

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 81531DiisopropylethylamineHCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 57726009HCID 57726009, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-chloropicolinoyl chloride hydrochloride (352 mg, 2.0 mmol, 1.0 eq) in 10 mL of THF were added N,N-dimethylhydrazine (120 mg, 2.0 mmol, 1.0 eq) and N,N-diisopropylethylamine (383 μL, 2.2 mmol, 1.1 eq) at room temperature. The reaction mixture was stirred for 15 min and diluted with water (25 mL) and EtOAc (50 mL). The separated organic layer was washed with brine (25 mL), saturated sodium bicarbonate solution (25 mL) and dried over sodium sulfate. Concentration under reduced pressure gave the title compound as colorless solid (223 mg, 56%), which was used without further purification. MH+=200, Rt=1.42 min.

Workup

  1. washThe separated organic layer was washed with brine (25 mL), saturated sodium bicarbonate solution (25 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-0240d0a608e34d5ab0923ee731b69644
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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