Hydrazinium chloride → 2,3,6,7-tetrahydro-5H-cyclopenta[d]pyridazine-1,4-dione

HRID 1479983Notes

Reaction equation

HRID 1479983 reaction equation
Cl.[NH2:2][NH2:3].[C:4]12[C:12](=[O:13])O[C:9](=[O:10])[C:5]=1[CH2:6][CH2:7][CH2:8]2>O>[C:9]1(=[O:10])[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:12](=[O:13])[NH:3][NH:2]1

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dione

Product 1

HCID 3263672,3,6,7-tetrahydro-5H-cyclopenta[d]pyridazine-1,4-dioneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of hydrazine hydrochloride (2.4 g, 22.8 mmol) and 1-cyclopentene-1,2-dicarboxylic anhydride (3.0 g, 21.7 mmol) in water (10 mL) is heated to reflux for 3 h. The reaction mixture is cooled down to room temperature and the precipitate is collected by filtration. The yellow solid is mixed with 15 mL 1N NaOH and stirred for 2 h, filtered and dried under vacuum to give 2,3,6,7-tetrahydro-5H-cyclopenta[d]pyridazine-1,4-dione (38) (2.2 g, 67%).

Workup

  1. temperatureto reflux for 3 h
  2. filtrationthe precipitate is collected by filtration
  3. additionThe yellow solid is mixed with 15 mL 1N NaOH
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2913fca0106347fe9f92ab6af69b4748
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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