Water → HCID 68424324, compound

HRID 1993496Notes

Reaction equation

HRID 1993496 reaction equation
[CH2:1]([CH:8]1[O:22][C:12]2=[CH:13][C:14]3[C:18]([CH:19]=[C:11]2[C:10](=O)[C:9]1=[O:24])=[N:17][C:16]([CH3:21])([CH3:20])[CH:15]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>CN(C=O)C.O.NN>[CH2:1]([CH:8]1[O:22][C:12]2=[CH:13][C:14]3[C:18](=[CH:19][C:11]2=[CH:10][C:9]1=[O:24])[NH:17][C:16]([CH3:21])([CH3:20])[CH:15]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 68424495HCID 68424495, compound

Product 1

HCID 68424324HCID 68424324, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-Benzyl-2,2-dimethyl-2H-pyrano[2,3-f]indole-7,8-dione (500 mg, 1.57 mmol) in DMF (5 mL), hydrazine monohydrate (2.5 mL) was added, and the resulting mixture was stirred at 100° C. for 1.5 hour. Water was added thereto, and the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with saturated aqueous ammonium chloride solution and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column (hexane/ethyl acetate=3/1) to obtain the aimed product (yield: 65%).

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe resulting organic phase was washed with saturated aqueous ammonium chloride solution
  3. dry with materialwith saturated sodium chloride solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7c97f663298841c0b2f32d46cb59d942
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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