Hydrochloric Acid → HCID 57621407, compound

HRID 490554Notes

Reaction equation

HRID 490554 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][NH:8][C:7]2=[O:13])([O-:3])=[O:2].[CH2:14](Br)[CH:15]=[CH2:16].[OH-].[Na+].Cl>O.[OH-].[K+]>[CH2:16]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7](=[O:13])[NH:8]1)[CH:15]=[CH2:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromide2×HCID 14798Sodium HydroxideHCID 53746612,3-Dihydro-5-nitro-1H-indazol-3-one

Product 1

HCID 57621407HCID 57621407, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
77.5 °C

Procedure

5-Nitro-1,2-dihydro-indazol-3-one (prepared according to Org. Synth. 1949, 29, 54 or Chem Ber. 1942, 75, 1104) (9.36 g) was suspended in 40 ml water and 57.5 ml 1N KOH. Allyl bromide (6.32 g) was added in one portion. The mixture was stirred at 75-80° C. for 1.5 hours. Then NaOH (15%, 5 mL) and allyl bromide (1 g) was added. The reaction mixture was stirred for a further 30 min. The mixture was neutralized with 3N HCl at <10° C. and filtered. The solid was washed with water and dried. The solid was then suspended in 10 ml ethyl acetate and stirred at ambient temperature for 3 hours, then filtered and dried to afford the desired 1-allyl-5-nitro-1,2-dihydro-indazol-3-one (7.63 g) as a yellow solid.

Workup

  1. stirringThe reaction mixture was stirred for a further 30 min
  2. filtrationfiltered
  3. washThe solid was washed with water
  4. customdried
  5. stirringstirred at ambient temperature for 3 hours
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-24d3449e796d4b4ca8df8581710e5e74
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

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