Potassium Hydroxide → HCID 67491631, compound

HRID 537169Notes

Reaction equation

HRID 537169 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[CH:9][CH:10]=2)[N:5](C(OCC)=O)[N:4]=1.[OH-].[K+]>C(O)C>[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67491844HCID 67491844, compound

Product 1

HCID 67491631HCID 67491631, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

1-Ethyl 6-methyl 3-methoxy-1H-indazole-1,6-dicarboxylate (444 mg, 1.60 mmol) was suspended in ethanol (5 mL). An aqueous solution of potassium hydroxide (16 mL, 16 mmol, 1 M) was added and the reaction was heated to 65° C. and stirred for 1.5 hours. The reaction was cooled to room temperature and concentrated. The residue was taken up in water and the solution was acidified with 1 N aqueous hydrochloric acid until a precipitate formed. The solid was collected by filtration, rinsed with water, and dried under vacuum to give the title compound (232 mg, 76%) as an orange solid. +ESI (M+H) 193.2; 1H NMR (400 MHz, DMSO-d6, δ): 12.22 (s, 1H), 7.90-7.94 (m, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.53 (dd, J=8.4, 1.4 Hz, 1H), 3.99 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-829714482c51437e9ce0974a14e44693
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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