Hydrochloric Acid → HCID 22479950, compound

HRID 1349650Notes

Reaction equation

HRID 1349650 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1.[OH:20]O.[OH-].[Na+].Cl>O.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([NH2:19])=[O:20])[CH:16]=3)[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22480119HCID 22480119, compound

Product 1

HCID 22479950HCID 22479950, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 20 mg (0.080 mmol) of 3-(4-methoxyphenyl)-1H-indazole-5-carbonitrile, 0.428 mL of 95% denatured ethanol, 0.021 mL of H2O, 0.32 mL of 30% aqueous hydrogen peroxide (aq. H2O2) and 0.032 mL of 6.0 N aq. NaOH (0.192 mmol, 2.4 equiv.) was heated at 50° C. for 3 h, and then acidified to pH=6.0 with 0.052 mL of 6.0 N 10 aq. HCl. The mixture was extracted with 2×EtOAc. The combined organics were washed with 2×sat. aq. NaHCO3, dried (Na2SO4), filtered, and concentrated affording the title compound (8.9 mg, 41.6% yield): 1H NMR (CDCl3/DMSO-d6) δ 12.5 (br s, 1H), 8.60 (s, 1H), 7.95 (d, 2H), 7.85 (d, 2H), 7.55 (d, 1H), 7.05 (d, 2H), 3.89 (s, 3H); ES-MS (m/z) 268 [M+1]+.

Workup

  1. extractionThe mixture was extracted with 2×EtOAc
  2. washThe combined organics were washed with 2×
  3. dry with materialaq. NaHCO3, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01130cb34ded4cfd8908c1376c452ac4
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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