Acetic Acid → 3-(4-Fluorophenyl)-1H-Indazole-5-Carboxylic Acid

HRID 1272754Notes

Reaction equation

HRID 1272754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=C(C#N)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[C:19]([OH:22])(=[O:21])[CH3:20].Cl>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:20]([C:19]([OH:22])=[O:21])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 222606703-(4-Fluorophenyl)-1H-indazole-5-carbonitrile

Product 1

HCID 222607223-(4-Fluorophenyl)-1H-Indazole-5-Carboxylic AcidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask containing 3-(4-fluorophenyl)-1H-indazole-5-carbonitrile (8.05 g, 0.034 mol) was added acetic acid (250 mL) and concentrated HCl (250 mL). The reaction was heated to reflux temperature for 7.5 hours and then 105° C. for two and one half-hours. The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and a solid crashed out of solution. The solid was collected by filtration and dried in a low temperature oven to yield the title compound (7.5 g, 86% yield). 1H NMR (DMSO-d6) δ 13.6 (br s, 1H), 13.0 (br s, 1H), 8.64 (s, 1H), 8.0–7.9 (m, 3H), 7.68 (d, 1H), 7.42 (t, 2H); ES-MS (m/z) 301 [M+1]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux temperature for 7.5 hours
  3. custom105° C.
  4. filtrationThe solid was collected by filtration
  5. customdried in a low temperature oven

Sources & evidence

ORD record
ord-9762c97f686448e79c9ce4c8b6d42700
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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