Acetic Acid → 6-Bromo-1,4-dihydroindeno[1,2-c]pyrazole

HRID 2377260Notes

Reaction equation

HRID 2377260 reaction equation
[H-].[Na+].[CH2:3](OC=O)C.[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=O)[CH2:13][CH2:12]2.O.[NH2:20][NH2:21].C(O)(=O)C>C1C=CC=CC=1>[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14]1[NH:20][N:21]=[CH:3][C:13]=1[CH2:12]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydrideHCID 5206955-Bromo-1-indanone

Product 1

HCID 596441466-Bromo-1,4-dihydroindeno[1,2-c]pyrazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of a 60% suspension of sodium hydride in mineral oil (6.83 g, 284.8 mmol) and ethylformate (24.2 mL, 284.8 mmol) in benzene (100 mL) at about 0° C. was added a solution of 5-bromo-1-indanone (30.0 g, 142.4 mmol) in benzene (100 mL) over about 90 minutes. The reaction was then stirred for about 17 hours while being allowed to warm to room temperature. The formed precipitate was collected by filtration and was dissolved in ethanol (600 mL). To this solution was added hydrazine monohydrate (17 mL, 350.5 mmol) and acetic acid (19.2 mL, 335.4 mmol) and the reaction mixture was heated under reflux for about 3 hours. The mixture was cooled, concentrated under vacuum and the precipitate was collected by filtration and was dried under high vacuum to provide the desired product. MS (DCI-NH3): m/z 235, 237 (M+H)+.

Workup

  1. filtrationThe formed precipitate was collected by filtration
  2. dissolutionwas dissolved in ethanol (600 mL)
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for about 3 hours
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated under vacuum
  7. filtrationthe precipitate was collected by filtration
  8. customwas dried under high vacuum

Sources & evidence

ORD record
ord-576a3542564741e6b10eaa89c5214378
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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