Hydrogen Peroxide → HCID 59352187, compound

HRID 2385540Notes

Reaction equation

HRID 2385540 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[C:4]2([C:24]3[C:15](=[CH:16][C:17]4[O:22][CH2:21][CH2:20][O:19][C:18]=4[CH:23]=3)[O:14][CH2:13]2)[C:3]1=[O:25].C(=O)([O-])[O-:27].[Na+].[Na+].OO>C(O)C>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([NH2:12])=[O:27])[C:5]=2[C:4]2([C:24]3[C:15](=[CH:16][C:17]4[O:22][CH2:21][CH2:20][O:19][C:18]=4[CH:23]=3)[O:14][CH2:13]2)[C:3]1=[O:25]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 59352298HCID 59352298, compound

Product 1

HCID 59352187HCID 59352187, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1′-methyl-2′-oxo-1,2,2′,3-tetrahydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indole]-4′-carbonitrile (0.25 g, 0.75 mmol) in ethanol (30 mL) was added saturated aqueous sodium carbonate (3 mL) and 30% w/w aqueous hydrogen peroxide (3 mL). The reaction mixture was heated at reflux for 3 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was triturated in water to afford 1′-methyl-2′-oxo-1′,2,2′,3-tetrahydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indole]-4′-carboxamide (0.09 g, 33%) as a colorless solid: mp>250° C. (water); 1H NMR (300 MHz, CDCl3) 7.59 (s, 1H), 7.43-7.36 (m, 1H), 7.24-7.13 (m, 3H), 6.28 (s, 1H), 5.98 (s, 1H), 5.15 (d, J=8.1 Hz, 1H), 4.57 (d, J=8.1 Hz, 1H), 4.16-3.99 (m, 4H), 3.13 (s, 3H); MS (ES+) m/z 352.9 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in water

Sources & evidence

ORD record
ord-12e76315f730435e9a70476f2574a6c1
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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