Hydrazine hydrate (1:1) → HCID 117770272, compound

HRID 1526323Notes

Reaction equation

HRID 1526323 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]([C:16]#[N:17])[C:5](=O)[N:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[CH3:14])[CH:7]=1.[OH2:19].[NH2:20][NH2:21].C(=O)([O-])O.[Na+]>C(O)C>[NH2:17][C:16]1[C:4]2[C:5](=[O:19])[N:6]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]3[CH3:14])[CH:7]=[C:2]([Br:1])[C:3]=2[NH:21][N:20]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 117770430HCID 117770430, compound

Product 1

HCID 117770272HCID 117770272, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-4-chloro-1-(2-methylcyclohexyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step F (1.29 g) in ethanol (20 mL) was added hydrazine monohydrate (0.288 mL) at room temperature. The reaction mixture was heated at 90° C. for 2 hr, and cooled to room temperature. The reaction mixture was poured into ice water, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.21 g).

Workup

  1. temperaturecooled to room temperature
  2. temperaturecooling
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a3d65597c42e4462b5d98bcd62c27c6a
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

Loading…