Hydrochloric Acid → HCID 22479895, compound

HRID 1349906Notes

Reaction equation

HRID 1349906 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=4)[NH:12][N:11]=3)[CH:8]=[CH:9][C:2]1=2.[OH:21]O.[OH-].[Na+].Cl>O.C(O)C>[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH2:20])=[O:21])[CH:17]=4)[NH:12][N:11]=3)[CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22479906HCID 22479906, compound

Product 1

HCID 22479895HCID 22479895, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-(2,3-dihydrobenzo[b]furan-5-yl)-1H-indazole-5-carbonitrile (0.50 g, 1.9 mmol), 95% ethanol (6 mL), 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 (40 mL) and acidified to pH 6 with 3 N hydrochloric acid. The solid was filtered and dried in a vacuum oven to give product (0.080 g, 53% yield): 1H NMR (DMSO-d6) δ 13.22 (s, 1H), 8.54 (s, 1H), 8.12 (s, 1H), 7.90 (d, 2H), 7.76 (d, 1H), 7.55 (d, 1H), 7.32 (s, 1H), 6.91 (d, 1H), 4.59 (t, 2H), 3.28 (t, 2H); ES-MS (m/z) 280 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-75878a227888414f9ae0c76795dde3b0
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…