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

HRID 989633Notes

Reaction equation

HRID 989633 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-9963a0a63c364fdba7853f5d31bdd9f4
Source dataset
uspto-grants-2002_10
Patent number
US06458771B1

Reaction notes

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