Water → N-Benzyl-6,6-dimethyl-1H-pyrano[2,3-f]indole-2-one

HRID 2425371Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-benzyl-6,6-dimethyl-1H-pyrano[2,3-f]indole-2,3-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 ammonium chloride aqueous 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

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

Sources & evidence

ORD record: ord-f2626dda8824429ab388fcfa5ad6b0e7
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964623B2

Reaction notes

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