Water → 2-tert-butoxycarbonyl-2,3-dihydro-1-methyl-6-nitro-1H-pyrazolo[4,3-c]quinolin-3-one

HRID 613473Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:23](=[O:24])[C:11]2[CH:12]=[N:13][C:14]3[C:15]([N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]=2[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[C:23](=[O:24])[C:11]2[CH:12]=[N:13][C:14]3[C:15]([N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]=2[N:9]1[CH3:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-tert-butoxycarbonyl-2,3-dihydro-6-nitro-1H-pyrazolo[4,3-c]quinolin-3-one (450 mg) and potassium carbonate (565 mg) in dimethylformamide was added methyl iodide (580 mg), and the mixture was stirred for 2 hours at 60° C. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane-ethyl acetate) to give 2-tert-butoxycarbonyl-2,3-dihydro-1-methyl-6-nitro-1H-pyrazolo[4,3-c]quinolin-3-one (114 mg).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel (dichloromethane-ethyl acetate)

Sources & evidence

ORD record: ord-20d13cec7a35481b8031dfa1ae4a7a69
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008230

Reaction notes

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