2H,5H-[1,3]Dioxolo[4,5-f]indole-6,7-dione → 3-(1-Methoxy-1-phenyl-methylidene)-5,6-methylenedioxy-2-indolinone

HRID 1007388Notes

Reaction equation

C([C:3](CC)(P(=O)([O-])[O-])[C:4]1(OC)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)C.C[C:19](C)([O-:21])C.[K+].[CH2:24]1[O:35][C:34]2[CH:33]=[C:32]3[C:28]([C:29](=O)[C:30](=[O:36])[NH:31]3)=[CH:27][C:26]=2[O:25]1>CN(C)C=O>[CH3:19][O:21][C:3](=[C:29]1[C:28]2[C:32](=[CH:33][C:34]3[O:35][CH2:24][O:25][C:26]=3[CH:27]=2)[NH:31][C:30]1=[O:36])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Under a nitrogen atmosphere 4.5 g of diethyl-1-methoxybenzylphosphonate (according to Burkhouse, D.; Zimmer, H.; Synthesis 1984, 330) are dissolved in 40 ml of absolute dimethylformamide and at −40° C. 4.0 g of potassium-tert-butoxide are added batchwise and stirred for 15 minutes at −10° C. 3.0 g of 5,6-methylenedioxyisatin (according to Lackey, K.; Sternbach, D. D.; Synthesis 1993, 993) are added to the clear solution and stirred for 1 hour at ambient temperature. After this time the mixture is poured into 20 ml of ice-cold saturated potassium hydrogen sulphate solution and extracted with ethyl acetate. The ethyl acetate phase is washed with water, dried over sodium sulphate and concentrated by evaporation. Finally the residue is separated through a silica gel column with toluene/ethyl acetate (5:1). The product obtained can be recrystallised from ether.

Workup

stirringstirred for 1 hour at ambient temperature
extractionextracted with ethyl acetate
washThe ethyl acetate phase is washed with water
dry with materialdried over sodium sulphate
concentrationconcentrated by evaporation
customFinally the residue is separated through a silica gel column with toluene/ethyl acetate (5:1)
customThe product obtained can
custombe recrystallised from ether

Sources & evidence

ORD record: ord-b2b46c844f114b12aaca447e40a18e13
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794395B1

Reaction notes

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