Sodium Hydroxide → 3-carbamoyl-1H-indazole-6-carboxylic acid

HRID 2403664Notes

Reaction equation

HRID 2403664 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1)#[N:2].OO.NC(N)=[O:20].[OH-].[Na+]>CO>[C:1]([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)(=[O:20])[NH2:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31294Carbamide PeroxideHCID 67491426methyl 3-cyano-1H-indazole-6-carboxylate

Product 1

HCID 708960233-carbamoyl-1H-indazole-6-carboxylic acidYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-cyano-1H-indazole-6-carboxylate (254 mg, 1.26 mmol) in methanol (12 mL) at 0° C. was added a cold solution of urea hydrogen peroxide (1.22 g, 12.6 mmol) in sodium hydroxide (12.6 mL 1M in water, 12.6 mmol). The yellow solution was stirred at room temperature overnight. The mixture was concentrated in vacuo to remove methanol. The pH of the resulting residue was adjusted to ˜4 with 1N hydrochloric acid. A precipitate formed. The mixture was filtered and the solid was dried to afford 3-carbamoyl-1H-indazole-6-carboxylic acid as a brown solid (82 mg, 32%). 1H NMR (400 MHz, DMSO-d6, δ): 13.84 (s, 1 H), 13.04 (br. s., 1 H), 8.20 (d, J=8.4 Hz, 1 H), 8.13-8.16 (m, 1 H), 7.77 (br. s., 1 H), 7.74 (dd, J=8.6, 1.4 Hz, 1 H), 7.38 (br. s., 1 H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove methanol
  3. customA precipitate formed
  4. filtrationThe mixture was filtered
  5. customthe solid was dried

Sources & evidence

ORD record
ord-ce2bd0c1fa7344dc859f4a8082c3f91b
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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