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

HRID 1406578Notes

Reaction equation

HRID 1406578 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].[K].[O-]CCCC.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 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 (I1b, 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 minutes. 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-d618c11c1d594aa1ae1ec940f8981fbc
Source dataset
uspto-grants-2014_12
Patent number
US08916600B2

Reaction notes

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