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

HRID 13181Notes

Reaction equation

HRID 13181 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-b3f2daa29ad240d2a9685cb893724806
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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