Hydrazine hydrate (1:1) → HCID 70005314, compound

HRID 1357326Notes

Reaction equation

HRID 1357326 reaction equation
C1(=O)[N:5]([CH2:6]/[CH:7]=[CH:8]/[CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11]2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH:7]=[CH:8][CH2:9][N:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18506023HCID 18506023, compound

Product 1

HCID 70005314HCID 70005314, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-[(E)-4-phthalimido-2-butenyl]-1H-imidazo[4,5-b]pyridine (2.19 g, 6.87 mmol) in ethanol (100 mL) at room temperature was treated with hydrazine monohydrate (3.33 mL, 68.7 mmol). After 10 min., the reaction mixture was warmed to 60° C. for 2 h, allowed to cool to 25° C., and recooled to 0° C. in an ice bath. The resulting slurry was filtered, and the filtrate was concentrated in vacuo. Purification by flash chromatography (6% NH4OH/ethanol) afforded 0.92 g of the title compound; mass (CI) m/z=211 (M+H).

Workup

  1. temperatureto cool to 25° C.
  2. customrecooled to 0° C. in an ice bath
  3. filtrationThe resulting slurry was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification by flash chromatography (6% NH4OH/ethanol)

Sources & evidence

ORD record
ord-9fee11a110b245d98a555e62a3b2874b
Source dataset
uspto-grants-2003_07
Patent number
US06590083B1

Reaction notes

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