Hydrochloric Acid → HCID 22480121, compound

HRID 1353958Notes

Reaction equation

HRID 1353958 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=3)[NH:15][N:14]=1)[CH:7]=[CH:6]2.[OH:24]O.[OH-].[Na+].Cl>O.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([NH2:23])=[O:24])[CH:20]=3)[NH:15][N:14]=1)[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22479712HCID 22479712, compound

Product 1

HCID 22480121HCID 22480121, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-(6-methoxy-2-naphthyl)-1H-indazole-5-carbonitrile (0.230 g, 0.77 mmol), 95% ethanol (6 mL), aqueous 30% hydrogen peroxide (3 mL), and 6.0 N aqueous sodium hydroxide (1 mL, mmol) was heated at 45° C. for 3 h. The reaction mixture was diluted with water (30 mL) and acidified to pH 6 with 3 N hydrochloric acid. The solid was filtered and dried in a vacuum oven to give product (0.050 g, 20% yield): 1H NMR (DMSO-d6) δ 13.45 (s, 1H), 8.72 (s, 1H), 8.50 (s, 1H), 8.18 (s, 1H), 8.15 (d, 1H), 8.02 (d, 1H), 7.95 (d, 1H), 7.61 (d, 1H), 7.37 (m, 2H), 7.22 (dd, 1H); ES-MS (m/z) 318 [M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-9e14655fa8fe4d25946b085d283e8718
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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