Sodium Hydroxide → 1-Methyl-1H-indazole-7-carboxylic acid

HRID 1908110Notes

Reaction equation

HRID 1908110 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13]C)=[O:12])[CH:4]=[N:3]1.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=[O:12])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 37818682Methyl 1-methyl-1H-indazole-7-carboxylate

Product 1

HCID 569730131-Methyl-1H-indazole-7-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 1-methylindazole-7-carboxylate (1 g, 5.3 mmol) was suspended in a mixture of sodium hydroxide (12 mL of 1.0 M, 12 mmol) and 1,4-dioxane (8.7 mL). The reaction mixture was heated at 80° C. for 30 minutes. The dioxane was evaporated off and the aqueous layer was extracted with ethyl acetate three times and the extracts were discarded. The aqueous layer was then acidified with 4M hydrochloric acid and then filtered and washed with 1M hydrochloric acid to yield 1-methylindazole-7-carboxylic acid (0.9 g, 97%) as a white solid. 1H NMR (400 MHz, DMSO) δ 13.31 (s, 1H), 8.20 (s, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.87 (d, J=7.2 Hz, 1H), 7.21 (t, J=7.6 Hz, 1H), 4.18 (s, 3H).

Workup

  1. customThe dioxane was evaporated off
  2. extractionthe aqueous layer was extracted with ethyl acetate three times
  3. filtrationfiltered
  4. washwashed with 1M hydrochloric acid

Sources & evidence

ORD record
ord-3521863a7c6641a99cadc6a101c696e0
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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