Hydrogen Peroxide → HCID 66604894, compound

HRID 2410677Notes

Reaction equation

HRID 2410677 reaction equation
C(=O)([O-])[O-:2].[Na+].[Na+].OO.[CH3:9][O:10][C:11]1[CH:23]=[C:22]2[C:14]([C:15]3[CH:16]=[C:17]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[CH:18]=[C:19]([C:24]#[N:25])[C:20]=3[NH:21]2)=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C>[CH3:9][O:10][C:11]1[CH:23]=[C:22]2[C:14]([C:15]3[CH:16]=[C:17]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)[CH:18]=[C:19]([C:24]([NH2:25])=[O:2])[C:20]=3[NH:21]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 66604959HCID 66604959, compound

Product 1

HCID 66604894HCID 66604894, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Aqueous sodium carbonate (3 M, 700 μL, 2.10 mmol) and aqueous hydrogen peroxide (30%, 700 μL, 6.79 mmol) were added to a suspension of 7-methoxy-3-(4-methoxyphenyl)-9H-carbazole-1-carbonitrile (69 mg, 0.21 mmol) in ethanol (10 mL). The mixture was heated overnight at 60° C. Sodium hydroxide (84 mg, 2.10 mmol) and additional aqueous hydrogen peroxide (30%, 700 μL, 6.79 mmol) were added and heating was continued for a further 17 hr. The ethanol was removed on the rotary evaporator and the white precipitate was collected by filtration, washed with water, and dried under vacuum. Silica gel radial chromatography using step gradient elution with hexane containing 25 to 100% ethyl acetate gave 7-methoxy-3-(4-methoxyphenyl)-9H-carbazole-1-carboxamide (41 mg, 54% yield) as a white solid. MS (ESI) m/z 347.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.21 (1H, s), 8.45 (1H, d, J=1.22 Hz), 8.29 (1H, br. s.), 8.13 (1H, d, J=1.53 Hz), 8.09 (1H, d, J=8.55 Hz), 7.80 (2H, d, J=8.55 Hz), 7.47 (1H, br. s.), 7.29 (1H, d, J=2.44 Hz), 7.07 (2H, d, J=8.55 Hz), 6.81 (1H, dd, J=8.55, 2.14 Hz), 3.84 (3H, s), 3.83 (3H, s).

Workup

  1. temperatureheating
  2. customThe ethanol was removed on the rotary evaporator
  3. filtrationthe white precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum
  6. washstep gradient elution with hexane containing 25 to 100% ethyl acetate

Sources & evidence

ORD record
ord-1672fdda171c4021a30afd2624b8c559
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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