Hydrochloric Acid → 3-(5-iodo-1H-indazol-1-yl)benzoic acid

HRID 1098942Notes

Reaction equation

HRID 1098942 reaction equation
F[C:2]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:3]=1[CH:4]=[N:5][NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].CC(C)([O-])C.[K+].Cl>CN1C(=O)CCC1.O>[I:20][C:17]1[CH:16]=[C:3]2[C:2](=[CH:19][CH:18]=1)[N:6]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])[N:5]=[CH:4]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 670412113-(2-(2-Fluoro-5-iodobenzylidene)hydrazinyl)benzoic acid

Product 1

HCID 574320973-(5-iodo-1H-indazol-1-yl)benzoic acidYield 107.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3-(2-(2-fluoro-5-iodobenzylidene)hydrazinyl)benzoic acid (3.47 g, 9 mmol) and potassium tert. butoxide (2.3 g, 20.5 mmol) was stirred under argon atmosphere in NMP (45 mL) at 150° C. for 30 min. After cooling, the mixture was diluted with water (100 mL), acidified with aqueous HCl (1.7 M) and extracted trice with EtOAc. The combined organic phases were washed twice with water and then with brine. Evaporation of the organic phase afforded crude title compound (3.52 g, quant.) as a light brown, amorphous, gummy solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted trice with EtOAc
  3. washThe combined organic phases were washed twice with water
  4. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-92df082fc27d4a2da25140b3ddd35e65
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

Loading…