Hydrazine hydrate (1:1) → HCID 68597755, compound

HRID 1407502Notes

Reaction equation

HRID 1407502 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][CH2:13][O:14][C:7]3=[CH:6][C:5]=2[C:4](=O)[C:3]1=[O:16].O.NN>O1CCOCC1.C(OCC)(=O)C>[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][CH2:13][O:14][C:7]3=[CH:6][C:5]=2[CH2:4][C:3]1=[O:16]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68598719HCID 68598719, compound

Product 1

HCID 68597755HCID 68597755, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-methyl-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione (3.00 g, 13.7 mmol) in 1,4-dioxane (25 mL) was added hydrazine monohydrate (25 mL). The reaction mixture was stirred at reflux for 4 h, allowed to cool to ambient temperature, diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was recrystallized from ethyl acetate/hexanes to afford 6-methyl-2,3,6,8-tetrahydro-7H-[1,4]dioxino[2,3-f]indol-7-one (2.46 g, 87%): 1H NMR (300 MHz, CDCl3) δ 6.75 (s, 1H), 6.49 (s, 1H), 4.19-4.12 (m, 4H), 3.36 (s, 2H), 3.00 (s, 3H); MS (ES+) m/z 206.2 (M+1).

Workup

  1. temperatureat reflux for 4 h
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8288a895fd1546f296262b9610213348
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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