Potassium tert-butoxide → 1H-indazole-6-carboxylic acid

HRID 2306665Notes

Reaction equation

HRID 2306665 reaction equation
CC(C)([O-])C.[K+].C(S/[N:12]=[N:13]/[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:17]([OH:19])=[O:18])(C)(C)C>CS(C)=O>[NH:13]1[C:14]2[C:22](=[CH:21][CH:20]=[C:16]([C:17]([OH:19])=[O:18])[CH:15]=2)[CH:23]=[N:12]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178425897HCID 178425897, compound

Product 1

HCID 162279381H-indazole-6-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of potassium tert-butoxide (8.1 g, 73 mmol) in DMSO (30 mL) was added a solution of 3-[(E)-(tert-butylthio)diazenyl]-4-methylbenzoic acid (1.9 g, 7.3 mmol) at RT. The mixture was stirred overnight, followed by the adition of ice water. The aqueous layer was extracted with ethyl acetate. The organic layer was dicarded. The pH of the aqueous layer was adjusted to 4-5 with aqueous 1N HCl. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 800 mg (97%) of 1H-indazole-6-carboxylic acid as a tan solid: 1H NMR (400 MHz. DMSO-d6) δ 13.4, 13.0, 8.2, 8.1, 7.9, 7.7.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60d1fea732414c9e9bb758150f81ad5b
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

Loading…