Hydrochloric Acid → 4-(5-Iodoindazole-1-yl)-benzoic acid

HRID 13177Notes

Reaction equation

HRID 13177 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:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.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:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)[N:5]=[CH:4]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 668129224-(2-(2-Fluoro-5-iodobenzylidene)hydrazinyl)benzoic acid

Product 1

HCID 593397454-(5-Iodoindazole-1-yl)-benzoic acidYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-(2-(2-fluoro-5-iodobenzylidene)hydrazinyl)benzoic acid (141d, 3.42 g, 8.9 mmol) and potassium tert-butoxide (2.29 g, 20.5 mmol) was stirred under argon atmosphere in NMP (45 mL) at 150° C. for 15 min. The mixture was then cooled, diluted with water and acidified with aqueous HCl (1.7 M). The precipitate that formed was collected by filtration and dried in vacuo to give crude 4-(5-iodo-1H-indazol-1-yl)benzoic acid (3.05 g, 94%)

Workup

  1. temperatureThe mixture was then cooled
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b0a180ffdb6a4a968061697b297c7dd0
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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