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

HRID 2204193Notes

Reaction equation

HRID 2204193 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-04b4497b2ea1402ab5f5f93340971a18
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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