Hydrazine hydrate (1:1) → 3-Chloroisoquinoline

HRID 1181408Notes

Reaction equation

HRID 1181408 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.O.NN>C(O)C>[Cl:12][C:4]1[N:3]=[CH:2][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2986251,3-Dichloroisoquinoline

Product 1

HCID 6409683-ChloroisoquinolineYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,3-dichloroisoquinoline (9.94 g, 50.2 mmol) and hydrazine hydrate (12.2 ml, 251 mmol) in ethanol (150 ml) was heated at reflux for 1.5 hours. The reaction was then cooled to room temperature and the ethanol evaporated. The residue was suspended in chloroform and manganese dioxide (20 g) was added in portions over 30 minutes. Gas evolution was observed. After this had subsided, the mixture was heated to reflux for 2 hours, then filtered and evaporated. Purification of the residue by flash column chromatography using dichloromethane as eluant gave the title compound (3.5 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customthe ethanol evaporated
  4. additionmanganese dioxide (20 g) was added in portions over 30 minutes
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 2 hours
  7. filtrationfiltered
  8. customevaporated
  9. customPurification of the residue by flash column chromatography

Sources & evidence

ORD record
ord-f1f46d3573494dd5b567d5bc24fb51c9
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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