Methanol → HCID 178434289, compound

HRID 1880369Notes

Reaction equation

HRID 1880369 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[CH:8]2)=[O:4].[Li+].[OH-].O.[CH3:17]O>>[CH3:17][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=2)[NH:10][N:9]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 22260640Methyl 1H-indazole-5-carboxylate

Product 1

HCID 178434289HCID 178434289, compoundYield 95%

Procedure

A solution of 1H-indazole-5-carboxylic acid methyl ester (8 g, 42.1 mmol), LiOH (5.05 g, 211 mmol), in methanol (100 mL) and water (35 mL) was stirred at room temperature for 20 hours. At the end of this time the reaction mixture was concentrated, the aqueous residue was acidified (pH˜6) using 10% aqueous citric acid (150 mL) and filtered the solid to obtain the crude product, which was washed with water (3×30 ml) and dried well to give the title compound (7 g, 95%) as a pale brown solid. 1H NMR (CDCl3): δ 8.5 (s, 1H), 8.0-8.1 (d, 1H), 7.45-7.55 (d, 1H), 2.5-2.66 (s, 3H),

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated
  2. filtrationfiltered the solid
  3. customto obtain the crude product, which
  4. washwas washed with water (3×30 ml)
  5. customdried well

Sources & evidence

ORD record
ord-dc917907ae6f437092cd9d929c3ac6ea
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

Loading…