Water → HCID 91373956, compound
Reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of tert-butyl(3-hydroxyphenyl)carbamate (3.02 g, 14.4 mmol) and potassium carbonate (2.99 g, 21.7 mmol) in N,N-dimethylformamide (35 mL) was added 2-chloro-5-nitropyridine (2.52 g, 15.9 mmol), and the mixture was stirred at 70° C. for 2 hr. To the reaction mixture was added water (100 mL), and the mixture was extracted with ethyl acetate (100 mL, 50 mL). The organic layer was washed with saturated brine (20 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give tert-butyl{3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate as a yellow solid. The obtained compound was used for the next reaction without further purification operation.
Workup
- extractionthe mixture was extracted with ethyl acetate (100 mL, 50 mL)
- washThe organic layer was washed with saturated brine (20 mL)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe insoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e0172add06e64f0d89686c7709eeb0f3
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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