Potassium Hydroxide → HCID 67491524, compound

HRID 880945Notes

Reaction equation

HRID 880945 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([O:14]C)=[O:13])[CH:8]=2)[N:3]1C(OCC)=O.[OH-].[K+]>C(O)C>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 67491561HCID 67491561, compound

Product 1

HCID 67491524HCID 67491524, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Ethyl 5-methyl 2-methyl-3-oxo-2,3-dihydro-1H-indazole-1,5-dicarboxylate (300 mg, 1.08 mmol) was dissolved in ethanol (4 mL). Potassium hydroxide (485 mg, 8.62 mmol) was added and the reaction was stirred at room temperature for 1.5 hours. LCMS showed the reaction to be incomplete. An aqueous solution of potassium hydroxide (10 mL, 10 mmol, 1.0 M) was then added and the reaction was heated to 65° C. for 2 hours. The reaction was cooled to room temperature and concentrated. The resulting orange solid was dissolved in water and acidified with 1 N aqueous hydrochloric acid. The precipitate was collected by filtration and dried under vacuum to give the title compound (158 mg, 76%) as a white solid. +ESI (M+H) 193.1; 1H NMR (400 MHz, DMSO-d6, δ): 12.75 (br. s., 1H), 11.06 (s, 1H), 8.15 (s, 1H), 7.99 (dd, J=8.7, 1.5 Hz, 1H), 7.28 (d, J=8.6 Hz, 1H), 3.37 (s, 3H).

Workup

  1. customthe reaction
  2. temperaturethe reaction was heated to 65° C. for 2 hours
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated
  5. dissolutionThe resulting orange solid was dissolved in water
  6. filtrationThe precipitate was collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bc55ebe516f7492aa60dac854846f3d6
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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