Hydrochloric Acid → HCID 86698655, compound

HRID 338308Notes

Reaction equation

HRID 338308 reaction equation
Cl([O-])=O.[Na+].[CH:5]([C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:24]#[N:25])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)=[O:6].O.P([O-])([O-])([O-])=[O:28].[Na+].[Na+].[Na+].OO.S([O-])([O-])=O.[Na+].[Na+].Cl>O.CC#N>[C:24]([C:12]1[CH:11]=[C:10]2[C:15]([C:7]([C:5]([OH:28])=[O:6])=[CH:8][NH:9]2)=[CH:14][C:13]=1[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)#[N:25]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 2196068527176-08-5HCID 23668197Sodium Chlorite2×HCID 86698654HCID 86698654, compound

Product 1

HCID 86698655HCID 86698655, compoundYield 119.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium chlorite (8.1 mg, 0.072 mmol) in water (2 mL) was added dropwise to a solution of 3-formyl-5-(4-methoxy-phenyl)-1H-indole-6-carbonitrile (50.0 mg, 0.18 mmol), sodium phosphate monohydrate (5.60 mg, 0.04 mmol) and 25% hydrogen peroxide (25.9 mg, 0.19 mmol) in MeCN (2 mL) and water (1 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes, and warmed to room temperature. Additional sodium chlorite (16.2 mg, 0.144 mmol) and MeCN (5 mL) were added, and the reaction mixture was stirred at room temperature for another 16 hours. The reaction was quenched with sodium sulfite (46.6 mg, 0.362 mmol) and acidified with concentrated HCl (1 mL) to form precipitates. The solid was filtered, washed with water (5 mL) and air dried to give the title compound (14 mg, 26% yield). MS (ES−) 291.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6) δ 12.35 (br. s., 1H), 12.14 (br. s, 1H), 8.29 (d, J=2.73 Hz, 1H), 8.07 (s, 1H), 8.04 (s, 1H), 7.50 (d, J=8.20 Hz, 2H), 7.08 (d, J=8.39 Hz, 2H), 3.83 (s, 3H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringthe reaction mixture was stirred at room temperature for another 16 hours
  3. customto form
  4. customprecipitates
  5. filtrationThe solid was filtered
  6. washwashed with water (5 mL) and air
  7. customdried

Sources & evidence

ORD record
ord-1ddebde999e54f97bcc3d1a4827978ad
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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