2-Methyl-6-nitroaniline → HCID 86713583, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:11]=1[NH2:12].CC(C)([O-])C.[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:12][C:11]2[C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=[CH:16][C:10]=2[CH3:9])=[N:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a solution of 5-bromo-2-chloropyrimidine (1.5 g, 7.89 mmol) and 2-methyl-6-nitroaniline (800 mg, 5.26 mmol) in N,N-dimethylformamide (10 mL) in a sealed tube was added potassium tert-butoxide (1.76 g, 15.78 mmol), and the mixture was heated under microwave at 130° C. for 2 hrs. LCMS showed the reaction was completed. The reaction was cooled to RT, quenched with water (20 mL) and extracted with ethyl acetate (3×100 mL). The organic layers were separated, combined, washed with water (50 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=10:1) to afford the title compound as a yellow solid (500 mg, 31%). MS (ES+) C11H9BrN4O2 requires: 309, 311. Found: 310, 312 [M+H]+.
Workup
- temperatureThe reaction was cooled to RT
- customquenched with water (20 mL)
- extractionextracted with ethyl acetate (3×100 mL)
- customThe organic layers were separated
- washwashed with water (50 mL) and brine (100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-8c7281fe31734810b7b3d219f6afe292
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126951B2
Reaction notes
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