Hydrazine hydrate (1:1) → HCID 89775215, compound

HRID 1526373Notes

Reaction equation

HRID 1526373 reaction equation
[Br:1][C:2]1[C:3](OC)=[C:4]([C:14]#[N:15])[C:5](=O)[N:6]([CH:8]([CH:10]2[CH2:12][CH2:11]2)[CH3:9])[CH:7]=1.[OH2:18].[NH2:19][NH2:20]>C(O)C>[NH2:15][C:14]1[C:4]2[C:5](=[O:18])[N:6]([CH:8]([CH:10]3[CH2:12][CH2:11]3)[CH3:9])[CH:7]=[C:2]([Br:1])[C:3]=2[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117769989HCID 117769989, compound

Product 1

HCID 89775215HCID 89775215, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1-(1-cyclopropylethyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step B of Example 163 (1.2 g), hydrazine monohydrate (1.01 g) and ethanol (20 mL) was stirred at 90° C. for 2 hr. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate). The residue was dissolved in ethyl acetate, and the solution was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.20 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate)
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-71a928203529439a8ebbb4e06aafbf6e
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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