Ammonium Hydroxide → HCID 57459596, compound

HRID 1020846Notes

Reaction equation

HRID 1020846 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([I:9])[CH:5]=[CH:4][N:3]=1.O.[NH2:11][NH2:12].[NH4+].[OH-]>O1CCOCC1.CCO>[Cl:8][C:7]1[C:2]([NH:11][NH2:12])=[N:3][CH:4]=[CH:5][C:6]=1[I:9]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 448870382,3-Dichloro-4-iodopyridine

Product 1

HCID 57459596HCID 57459596, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of intermediate compound D6 (8 g, 29.21 mmol) in 1,4-dioxane (450 ml), was added hydrazine monohydrate (14.169 ml, 175.255 mmol). The reaction mixture was heated in a sealed tube at 80° C. for 16 h. After cooling, NH4OH (32% aqueous solution) was added to the reaction mixture, which was then concentrated in vacuo. The white solid residue thus obtained was taken up in EtOH and heated. The suspension thus obtained was allowed to cool down and the precipitate obtained was filtered off, washed with EtOH and dried in the desiccator to yield intermediate compound D7 (2.67 g, 52%) as a white solid

Workup

  1. temperatureAfter cooling
  2. concentrationwas then concentrated in vacuo
  3. customThe white solid residue thus obtained
  4. temperatureheated
  5. customThe suspension thus obtained
  6. temperatureto cool down
  7. customthe precipitate obtained
  8. filtrationwas filtered off
  9. washwashed with EtOH
  10. customdried in the desiccator

Sources & evidence

ORD record
ord-b1f55313fb304fa7a06e8b91207be2bc
Source dataset
uspto-grants-2014_05
Patent number
US08716480B2

Reaction notes

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