Hydrochloric Acid → HCID 22479727, compound

HRID 1349901Notes

Reaction equation

HRID 1349901 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=4)[NH:13][N:12]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH:22]O.[OH-].[Na+].Cl>O.C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]([NH2:21])=[O:22])[CH:18]=4)[NH:13][N:12]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22480165HCID 22480165, compound

Product 1

HCID 22479727HCID 22479727, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-(2H,3H-benzo[e]1,4-dioxin-6-yl)-1H-indazole-5-carbonitrile (0.230 g, 0.83 mmol), 95% ethanol, aqueous 30% hydrogen peroxide (3 mL), and 6.0 N aqueous sodium hydroxide (1 mL) was heated at 45° C. for 3 h. The reaction mixture was diluted with water (80 mL) and acidified to pH 6 with 3 N hydrochloric acid. The solid was filtered and dried in a vacuum oven and gave the title compound (0.098 g, 50% yield): 1H NMR (DMSO-d6) δ 13.31 (s, 1H), 8.55 (s, 1H), 8.17 (br s, 1H), 7.92 (d, 1H), 7.57 (d, 1H), 7.52 (m, 2H), 7.31 (br s, 1H), 7.02 (d, 1H), 4.32 (s, 4H); ES-MS (m/z) 296 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-0fa8392870a14212921c34949e3c19f3
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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