Hydrazine → HCID 178514300, compound

HRID 2104132Notes

Reaction equation

HRID 2104132 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[C:9]([OH:11])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[N:18]=1.[NH2:19][NH2:20].O1CCOCC1>C(OCC)(=O)C>[NH:19]([C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:18]=1)=[N:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:9]([OH:11])[N:10]=2)[NH2:20]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 312751,4-DioxaneHCID 178517175HCID 178517175, compound

Product 1

HCID 178514300HCID 178514300, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a flask was added 6-chloro-3-phenylpyrido[2,3-b]pyrazin-2-ol (8-2, 3.41 g, 13.23 mmol), anhydrous hydrazine (5.0 mL, 159 mmol), and finally 1.4 Dioxane (60 mL). The stirred reaction mixture was then heated to 100° C. in a hot oil bath under an atmosphere of nitrogen with an air cooled reflux condenser attached. Upon completion of the reaction the mixture was cooled to room temperature, suspended in ethyl acetate and washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 8-3 as an orange/tan foam. HRMS (M+H)+: observed=254.1041, calculated=254.1037.

Workup

  1. customThe stirred reaction mixture
  2. temperaturecooled
  3. temperaturereflux condenser
  4. customUpon completion of the reaction the mixture
  5. temperaturewas cooled to room temperature
  6. washwashed with a saturated solution of sodium bicarbonate
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24870a4d9b304e21ac388ce7078d7cd8
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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