Hydrochloric Acid → 3-(3,4-dimethoxyphenyl)-1H-indazole-5-carboxamide

HRID 1349713Notes

Reaction equation

HRID 1349713 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=3)[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-:22].[Na+].OO.Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([NH2:21])=[O:22])[CH:18]=3)[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 224800333-(3,4-dimethoxyphenyl)-1H-indazole-5-carbonitrile

Product 1

HCID 224798473-(3,4-dimethoxyphenyl)-1H-indazole-5-carboxamideYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3,4-dimethoxyphenyl)-1H-indazole-5-carbonitrile (200 mg, 0.72 mmol) in ethanol (3.5 mL) was added 6 N NaOH (0.5 mL) followed by H2O2 (2.0 mL of a 30% solution). The solution was heated to 45° C. for 1 hour when water (80 mL) was added and the pH adjusted to <1 with 3 N HCl. The reaction was then filtered and the product dried to give the title compound (180 mg, 61 mmol, 84% yield). 1H NMR (DMSO-d6) δ 13.3 (s, 1H), 8.59 (s, 1H), 8.12 (br s, 1H), 7.92 (d, 1H), 7.6–7.5 (m, 2H), 7.52 (s, 1H), 7.3 (br s, 1H), 7.13 (d, 1H), 3.87 (s, 3H), 3.84 (s, 3H); ES-MS (m/z) 298 [M+1]+.

Workup

  1. additionwas added
  2. filtrationThe reaction was then filtered
  3. customthe product dried

Sources & evidence

ORD record
ord-3dccd52a5a95478b80fb799d830fc19a
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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