Hydrogen Peroxide → Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate
Reaction equation
[NH2:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].OO.C(=O)([O-])[O-:18].[K+].[K+]>CS(C)=O>[NH2:1][C:2]1[C:3]([C:13]([NH2:14])=[O:18])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]Participants
Procedure
Methyl 5-amino-4-cyano-2-methylbenzoate (151 mg, 0.79 mmol) (synthesized according to reagent preparation 41) was dissolved in DMSO (1.5 mL). 30% Aqueous hydrogen peroxide (0.3 mL) and potassium carbonate (35 mg, 0.25 mmol) were added, and the mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted (2×) with ethyl acetate. The combined organic portion was dried over sodium sulfate, filtered and concentrated to a yellow oil which was purified by preparative reverse phase HPLC to afford methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate (108 mg, 0.52 mmol, 66% yield). NMR (400 MHz, CDCl3): δ 7.85 (s, 1H), 7.45 (br s, 1H), 7.26 (s, 1H), 7.19 (br s, 1H), 6.48 (s, 2H), 3.80 (s, 3H), 2.32 (s, 3H); MS (EI) for C10H12N2O3: 209 (MH+).
Workup
- customThe reaction mixture was partitioned between ethyl acetate and water
- extractionThe aqueous portion was extracted (2×) with ethyl acetate
- dry with materialThe combined organic portion was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated to a yellow oil which
- customwas purified by preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-681ce2a519fd405591d2cd681d47038d
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012956B2
Reaction notes
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