Potassium Hydroxide → HCID 67491371, compound

HRID 880981Notes

Reaction equation

HRID 880981 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14]C)=[O:13])=[CH:7][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][C:6]([C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67491533HCID 67491533, compound2×

Product 1

HCID 67491371HCID 67491371, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 1-ethyl 6-methyl 2-methyl-3-oxo-2,3-dihydro-1H-indazole-1,6-dicarboxylate (formed in Step 3 of Intermediate 28) (514 mg, 1.85 mmol) in ethanol (6 mL) was added 1 N aqueous potassium hydroxide (18.5 mL, 18.5 mmol). The reaction was heated to 65° C. for 1.5 hours. The reaction was cooled to room temperature and concentrated to dryness. The residue was taken up in water and acidified with 1 N aqueous hydrochloric acid until a precipitate formed. The solid was collected by filtration and dried under vacuum to give the title compound (196 mg, 55%) as a brown solid. 1H NMR (400 MHz, DMSO-d6, δ): 13.12 (br. s., 1H), 10.61 (br. s., 1H), 7.76 (s, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.60 (dd, J=8.2, 1.2 Hz, 1H), 3.38 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customformed
  4. filtrationThe solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3b79489e864c4b2a802655de600cd629
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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