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Hydrazine hydrate (1:1) → HCID 66784143, compound

HRID 1841971
Notes
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Reaction equation

HRID 1841971 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([Cl:9])[CH:5]=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>O1CCOCC1.C(Cl)Cl>[Cl:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:11][NH2:12])[C:7]=1[I:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 106360172,4-Dichloro-3-iodopyridine

Product 1

HCID 66784143HCID 66784143, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,4-dichloro-3-iodopyridine [CAS 343781-36-3] (4.7 g, 17.16 mmol) in 1,4-dioxane (240 ml), was added hydrazine monohydrate (5.096 ml, 102.962 mmol). The reaction mixture was heated in a sealed tube at 80° C. for 16 h. After cooling, the solvent was concentrated in vacuo. The white solid residue thus obtained was dissolved in DCM and washed with NaHCO3 (aqueous saturated solution). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The residue was washed with Et2O. The solid thus obtained was discarded. The mother liquours were concentrated in vacuo to yield intermediate compound D32 (2.31 g, 49%)

Workup

  1. temperatureAfter cooling
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe white solid residue thus obtained
  4. washwashed with NaHCO3 (aqueous saturated solution)
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. washThe residue was washed with Et2O
  9. customThe solid thus obtained
  10. concentrationThe mother liquours were concentrated in vacuo
  11. customto yield intermediate compound D32 (2.31 g, 49%)

Sources & evidence

ORD record
ord-17b56f207eac483f93e75b4f4e77a5ef
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946205B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes